JPH01125345A - プロペン酸誘導体の製造方法 - Google Patents

プロペン酸誘導体の製造方法

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Publication number
JPH01125345A
JPH01125345A JP63224813A JP22481388A JPH01125345A JP H01125345 A JPH01125345 A JP H01125345A JP 63224813 A JP63224813 A JP 63224813A JP 22481388 A JP22481388 A JP 22481388A JP H01125345 A JPH01125345 A JP H01125345A
Authority
JP
Japan
Prior art keywords
methyl
formula
mixture
salt
copper
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP63224813A
Other languages
English (en)
Other versions
JP2780786B2 (ja
Inventor
Kevin Beautement
ケビン・ビユートメント
John M Clough
ジヨン・マーチン・クロウ
Christopher R A Godfrey
クリストフアー・リチヤード・アイレス・ゴツドフレイ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GB878721221A external-priority patent/GB8721221D0/en
Priority claimed from GB878722537A external-priority patent/GB8722537D0/en
Priority claimed from GB888804433A external-priority patent/GB8804433D0/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of JPH01125345A publication Critical patent/JPH01125345A/ja
Application granted granted Critical
Publication of JP2780786B2 publication Critical patent/JP2780786B2/ja
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
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    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
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    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
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    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
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Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。

Description

【発明の詳細な説明】 本発明は殺菌剤として有用であるか又は殺菌剤を製造す
る際の化学的中間体として有用であるプロペン酸の誘導
体の製造方法に関する。
本発明によると、次式（ＩＩ）： （式中Ｘはハロゲン、好ましくはヨウ素、塩素又は臭素
である）の化合物を塩基の存在下に次式（）： のフェノールと又はフェノール（ＩＩＩ）の塩と、好ま
しくは適当な遷移金属、遷移金属塩又は化合物又はこれ
の混合物よりなる触媒の存在下に反応させるごとからな
る、次式（Ｉ）： （式中ベンゼン環Ｍ及びＮは場合によっては、不法の条
件下で反応性でない置換基の１個又はそれ以上を担持す
る）のプロペン酸化合物の製造方法が提供される。
この方法においては、式（ＩＩ）のフェノールを塩基で
前もって処理することにより該フェノールから誘導した
塩と化合物（ＩＩ）を反応させることにより式（１）の
化合物が得られる。本発明のこの要旨では、カップリン
グ反応中に塩基を追加的に存在させることは必要でない
。
不法を行なうのに溶剤を使用できる。適当な溶剤は両方
の化合物（ＩＩ）及び（■）（又はこれから誘導した塩
）が可溶性又は部分的に可溶性でしかも反応条件下でこ
れらの原料基剤の何れとも反応しない溶剤である。用い
得る溶剤には双極性の非プロトン溶剤例えばＮ、Ｎ−ジ
メチルホルムアミド、ジメチルスルホキシド、Ｎ、Ｎ−
ジメチルアセトアミド及びメチルイソブチルケトンがあ
る。成る場合には、原料基剤の何れかが反応条件下で液
体である時には、溶剤を追加的に存在させることなく反
応を行ない得る。
不法で用いるに適当な塩基は、原料基剤（Ｉｔ）との反
応前に化合物（Ｉ［［）のフェノール系プロトンの抽出
によりあるいは原料基剤（ＩＩ）又は生成物（１）と有
意な程に反応することなく反応中に生じた酸の中和によ
り作用する塩基である。か−る塩基の例は無水の炭酸カ
リウムである。
不法を触媒反応させ得る適当な遷移金属又は遷移金属塩
又は化合物には銅金属、銅塩及び化合物及びニッケル塩
及び化合物例えば青銅（ｃｏｐｐｅｒ　ｂｒｏｎｚｅ）
及び塩化銅（１）があり、これは別個に又は混合して用
い得る（例えばＡ、Ａ　Ｍｏｒｏｚ及びＭ、ＳＳｈｖａ
ｒｔｓｂｅｒｇのＲｕ５ｓｉａｎ　Ｃｈｅｍｉｃａｌ　
Ｒｅｖｉｅｗｓ、　１９７４＋邦（８）、　６７９〜６
８９参照）。
不法は広範囲の温度に亘って実施できる。実際には温度
は反応が適当な且つ都合の良い速度で生起するように選
ばれる。この温度は原料基剤（ＩＩ）及び（ＩＩＩ）の
反応性及び触媒の種類に応じて通常１００℃〜２００℃
の範囲にあるものである。
プロペノエート二重結合が存在すると化合物Ｎ）及び（
ＩＩ）の幾何異性体を生ずる。これらの異性体は文献（
例えばＪ、　Ｍａｒｃｈの’　ＡｄｖａｎｃｅｄＯｒｇ
ａｎｉｃ　Ｃｈｅｍｉｓｔｒｙ”　３版、Ｗｉｌｅｙ−
Ｉｎｔｅｒｓｃｊｅｎｃｅ＋１０９頁以降を参照された
い）に十分に記載されたカーノ・インゴールド・プレロ
グ（Ｃａｈｎ−１ｎｇｏｌｄ−Ｐｒｅｌｏｇ）系により
通常用いた用語（Ｅ）及び（Ｚ）により表わされる。一
般式（ＴＩ）の化合物の（ＩＥ）−異性体又は（Ｚ）−
異性体の何れか又はこれらの混合物は本発明の方法で原
料基剤として使用できる。反応条件下で一般式（Ｉｌ）
の化合物の（ｚ）−異性体は通常対応の（Ｅ）−異性体
への立体変異を受け、反応は（Ｅ）−配置の式（Ｔ）の
化合物を与えるように進行するものである。即ち、（Ｅ
）−配置の式（１）の化合物が式（ｎ）の前駆体の配置
に拘らず通常形成される。
本発明の方法は殺菌性化合物の製造に特別の有用性を有
しており；例えば欧州特許出願公開Ｅｐ−Ａ−０１７８
８２６に記載された化合物、特に一般式（ｒＶ）の化合
物の製造に有用性を有する： 〔式中Ａ、Ｂ、Ｄ及びＹは同じでも異なっても良く、水
素又はハロゲン原子であり又は随意に置換したアルキル
、随意に置換したアルケニル、随意に置換したアリール
、随意に置換した複素アリール、随意に置換したアルキ
ニル、随意に置換したアルコキシ、随意に置換したアリ
ールオキシ、随意に置換した複素アリールオキシ、随意
に置換したアリールアルコキシ、随意に置換したアシル
オキシ、随意に置換したスルホニルオキシ、随意に置換
したアミノ、随意に置換したアリールアゾ、アシルアミ
ノ、ニトロ、シアノ、−ＣＯ□Ｒ１、−ＣＯＮＲ２Ｒ３
、−ＣＯＲ’　、−ＣＲ５＝ＮＲ６又は−Ｎ＝ＣＲ’Ｒ
８基であるか、あるいは基Ａ及びＢはこれらがフェニル
環上の隣接位置にある時は結合して１個又はそれ以上の
異原子を場合によっては含有する縮合環を形成でき；Ｒ
１、Ｒ２、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７及びＲ８は同
じでも異なっても良く水素原子又はアルキル、シクロア
ルキル、アルケニル、アルキニル、随意に置換したアリ
ール、随意に置換した複素アリール、随意に置換したア
ラルキル又はシクロアルキルアルキル基である〕。
末法を用いて殺菌剤の製造に有用な化学的中間体を製造
できる。
一般式（Ｉ［）の原料基剤はＥＰ−Ａ−０１７８８２６
に概略した方法により製造できる。
一般式（Ｉ［［）の化合物は化学文献に記載される如き
既知の方法によって製造できる。
次の実施例は本発明を例示するものである。これらの実
施例を通して、水感作性中間体を使用する反応は無水溶
剤中で窒素の雰囲気下で実施し、用語「エーテル」はジ
エチルエーテルを表わし、硫酸マグネシウムを用いて溶
液を乾燥させ溶液は減圧下に濃縮し、クロマトグラフィ
ーはシリカゲルのカラム上で実施した。但し書きがなけ
ればｎ、ｍ、ｒスペクトルは重クロロホルム溶液と内部
標準品としてのテトラメチルシランとを用いて２７０Ｍ
Ｈｚで記録した。分光データが示されていても選択的で
あり、全ての場合にあらゆる吸収を挙げるようにした訳
ではない。
次の略号を用いる： ＩＲ＝赤外、ｎ、＋ｎ、ｒ　＝核磁気共鳴、ＭＳ−質量
分光法、ＧＣ＝ガスクロマトグラフィー、Ｓ＝−重積、
ｄ＝二重重積を−三重積、ｍ−多重積、ｂｒ＝ブロード
、ｍ、ｐ−融点、ｐ、ｐｍ＝パートバーミリオン、ＤＭ
Ｆ　＝Ｎ、Ｎ−ジメチルホルムアミド実施■実 施 本土施例は（Ｅ）−メチル　３−メトキシ−２−［２−
（３−メチルフェノキシ）フェニル１プロペノニー１〜
の製造を例示するものである。
５滴の濃硫酸を含有する無水メタノール（４０ｍＲ）に
溶かしたオルト−ブロムフェニル酢酸（５，１４ｇ）の
溶液を３時間加熱還流させた。反応混合物を冷却し、次
いで氷水（１５０ｍ）にそ＼ぎ、エーテル（２Ｘ７５ｍ
ｊりで抽出した。エーテル相を合し、水（×３）、重炭
酸ナトリウム飽和溶液（×２）、水（×１）及び飽和ブ
ラインで連続的に洗浄し、次いで乾燥させた。濾過及び
蒸発させると淡黄色液体、ＩＲ最大値１７４２ｃ「’、
としてメチル　０−ブロムフェニルアセテート　（５，
２３ｇ、　９６％）を得、これは更に精製することなく
使用した。
ＤＭＦ（６ｍｆｆｉ）に入れたメチル　０−ブロムフェ
ニルアセテート　（５，２３ｇ　）とメチルホルメート
（２７，４６ｇ）との混合物を、０〜５℃でＤＭＦ（４
５＋＋Ｉｌ）に入れた水素化ナトリウム（１，１０ｇ）
の攪拌懸濁液に滴加した（起泡した）。反応が完了した
ことを薄層クロマトグラフィーが示した後に、該混合物
を水にそ＼ぎ、酸性化し、エーテルで抽出した。抽出液
を乾燥させ、濃縮すると黄色液体として粗製のメチル　
２−（２−ブロムフェニル）−３−ヒドロキシプロペノ
エート　（５，９５ｇ　）が得られ、これを次の工程に
直接用いた。粗製のメチル　２−（２−ブロムフェニル
）−３−ヒドロキシプロペノエート　（５，９５ｇ　）
を、ＤＭＦ（４Ｍ）に入れた無水炭酸カリウム（６，３
８ｇ）及び硫酸ジメチル（２，７５ｇ　）と共に攪拌し
た。
室温で３時間後に、反応混合物を水にそ−ぎ、エーテル
（２Ｘ７５ｄ）で抽出した。合したエーテル相を水及び
ブライン（×１）で洗浄し、乾燥させた。
濾過及び蒸発させると黄色油が得られこれは放置すると
晶出して結晶質固体として（Ｅ）−メチル　２−（２−
ブロムフェニル）−３−メトキシプロペノエート（５，
２０ｇ　、メチル　０−ブロムフェニルアセテートから
８８％の収率）を得た、ｍ、ｐ、６８〜６９℃１ＩＦ？
最大（Ｊ１７１２＋　１６３８ｃｒｎ　’　；　’Ｈｎ
、ｍ、ｒδ３．７２（３Ｈ，Ｓ）　；３．８６（３Ｈ，
ｓ）；　７．５６（ＩＩ、　ｓ）　ｐｐｎ＋。
炭酸カリウム（２６０ｍｇ）と（Ｅ）−メチル　２−（
２−ブロムフェニル）−３〜メトキシプロペノエート（
２５０■）と塩化銅（Ｉ）（触媒量）とを３−メチルフ
ェノール（２１０■）に連続的に添加した。得られる混
合物を攪拌しながら１７０℃で３．５時間加熱し次いで
放冷した。該混合物をＤＭＦＣ３ｍＲ）に溶解し、次い
で水にそ＼ぎ、希塩酸で酸性化し次いでエーテル（３×
２５ｍｆｉ）で抽出した。合した抽出液を水酸化ナトリ
ウム水溶液（×３）次いで水（×２）及びブラインで完
全に洗浄し次いで乾燥した。得られる溶液を濃縮し、溶
離液として石油留分中の３０％エーテルを用いてクロマ
トグラフィーにかけると白色の結晶質固体として標記化
合物（１２０ｍｇ、４２％の収率）を得た、ｍ、ｐ、７
９〜８０℃５Ｉｔ？最大値１７１１．１６３２ｃｍ−’
Ｈ’Ｈｎ、ｍ、ｒδ２．３０（３Ｉ（、ｓ）　；３．６
２（３）１．　ｓ）；　３．７７（３Ｈ，ｓ）；７．４
８（ＩＩ（、ｓ）　ｐ、ｐ、ｍ。
実皇桝１ 本実施例は（Ｅ）−メチル　３−　［２−（３−クロル
フェノキシ）フェニル］−３−メトキシプロペノエート
の製造を例示するものである。
ナトリウム（６６■）を窒素下に無水メタノール（２ｄ
　）に溶解させた。３−クロルフェノール（３７２■）
を１回で添加すると黄色溶液を得、これを室温で４５分
間攪拌した。メタノールを蒸発させると黄色油を得、（
Ｅ）−メチル２−（２−ブロムフェニル）−３−メトキ
シプロペノエート（３００＋ｎｇ、実施例１に記載した
如く製造した）及び触媒量の青銅を添加した。得られる
混合物を１５０℃で２時間、１７０　’Ｃで２時間加熱
した。触媒量の塩化銅（１）を添加し、１５０　’Ｃで
の加熱を更に２時間続行した。この段階で反応混合物を
ＧＣ／ＭＳにより分析すると該混合物は幾つかの生成分
（該混合物の５％以下）と−緒に未反応の（Ｅ）−メチ
ル２−（２−ブロムフェニル）−３−メトキシプロペノ
エート（３７％）と３−（３−クロルフェノキシ）フェ
ノール（１５％）と標記化合物（２６％）とからなるこ
とを示した。
尖隻貫主 本実施例は（Ｅ）−メチル　３−メトキシ−２−［２−
（３−メチルフェノキシ）フェニル］　プロペノエート
の別の製造を例示するものである。
メチル　０−ブロムフェニルアセテート（４，１０ｇ　
。
実施例１に記載された如く製造した）と二酸化セレン（
４，２９ｇ　）との混合物を１９０″Ｃで２５時間攪拌
した。冷却後に該混合物をジクロルメタン（１００ｍＲ
）で希釈し次いで「スーパーセル」に通して濾過した。
濾液を重炭酸ナトリウムの飽和水溶液（×２）及びブラ
インで連続的に洗浄し、次いで乾燥し、濃縮させるとメ
チル（２−ブロムベンゾイル）ホルメートと未反応のメ
チル　０−ブロムフェニルアセテートとを含有する（Ｇ
Ｃ−ＭＳにより５２％）黄色液体（３，６０ｇ　）を得
た。
カリウム　ｔ−ブトキシド（２，３３ｇ　）を、室温で
エーテル（８０ｄ）中の（メトキシメチル）トリフェニ
ルホスホニウム　クロライド（７，９０ｇ　）の激しく
攪拌した懸濁液に添加した。１５分後に、エーテル（１
０ｄ）に溶かした粗製のメチル（２−ブロムベンゾイル
）ホルメート（３，６０ｇ）の溶液を１回で添加した。
更に１５分後に、反応混合物を水（１５Ｍりにそ＼ぎ、
水性相と有機相とを分離し、水性相を別置のエーテル（
１００ｍｆ）で抽出した。合したエーテル相を水（×２
）及びブラインで連続的に洗浄し、次いで乾燥し、濃縮
すると、約６：５の比率でそれぞれメチル２−（２−ブ
ロムフェニル）−３−メトキシプロペノエートの（Ｅ）
−異性体及び（Ｚ）−異性体を含有する黄色油（５，８
１ｇ）を得た。溶離液としてエーテルニヘキサン（１：
１）を用いてクロマトグラフィーにかけると淡黄色油と
して純粋な（Ｚ）−異性体（０，４５０ｇ　）を単離で
きた、ＩＲ（フィルム）１７１２、１６３８ｃｍ−’、
’Ｈｎ、ｍ、ｒδ３．７１（３Ｈ，ｓ）、　３．９５（
３８，ｓ）＋　６．５７（１）１．　ｓ）　ｐｐｍ。
（Ｚ）−メチル２−（２−ブロムフェニル）−３−メト
キシプロペノエート（０，３７０ｇ）と３−メチルフェ
ノール（０，２９４ｇ　）と炭酸カリウム（０，３３７
ｇ　）　と塩化銅（Ｉ）（触媒量）との混合物を１７０
″Ｃに加熱した。
４５分後に、この混合物をＧＣ及び薄層クロマトグラフ
ィーにより分析するとそれがおよそ等量の（Ｅ）−メチ
ル２−（２−ブロムフェニル）−３−メトキシプロペノ
エートと標記化合物とを含有し、原料の（Ｚ）−メチル
２−（２−ブロムフェニル）−３−メトキシプロペノエ
ートの何れも検出されないことを示した。更に３．２５
時間後に、反応混合物を放冷し、ＤＭＦ（５ｄ）に溶解
し、次いで水で希釈し、希塩酸で酸性化し、エーテルで
抽出した。これらの抽出液を水酸化ナトリウムの水溶液
（×３）、水（×２）及びブラインで連続的に洗浄し、
次いで乾燥し、濃縮し、溶離剤としてエーテル：ヘキサ
ン（１：　１）を用いてクロマトグラフィーにかけると
灰白色の固体として標記化合物（０，１１０ｇ、２７％
の収率）を得、その分光測定データは実施例１の標記化
合物についてと同じであった。
尖施侃土 本実施例は（Ｅ）−メチル　３−メトキシ−２−（２−
［３−（４−フェノキシフェノキシ）フェノキシ１　フ
ェニル］プロペノエートの製造を例示するものである。
３−（４−フェノキシフェノキシ）フェノール（４，１
１ｇ）と（Ｅ）−メチル２−（２−ブロムフェニル）−
３−メトキシプロペノエート（２，０ｇ、実施例１に記
載した如く製造した）と炭酸カリウム（２，０４ｇ　）
と塩化銅（Ｉ）（０，１ｇ）との混合物を１７０〜１８
０℃で４時間攪拌し次いで放冷した。
該混合物を水で希釈し、エーテルで抽出した。
エーテル抽出液を水酸化ナトリウム水溶液及びブライン
で連続的に洗浄し、次いで乾燥させ、濃縮すると褐色ゴ
ム状物（４，４７ｇ　）を得た。このゴム状物を、溶離
液としてヘキサン中に種々の割合（２０％）のエーテル
を用いてクロマトグラフィーにかけるとコハク色のゴム
状物として標記化合物（２，０６ｇ、６０％）を得た。
’Ｈｎ、ｍ、ｒ　（９０ＭＨｚ）δ：　３．６２（３Ｌ
　ｓ）、　３．７７（３Ｎ、　ｓ）、　６．６４〜７．
４９（１７）１゜ｍ）＋　７．５０（ＬＨ，ｓ）　ｐｐ
ｍ。
尖隻拠１ 本実施例は（Ｅ）−メチル　３−メトキシ−２−（２−
［３−（３−ニトロフェノキシ）フェノキシ１　フェニ
ル）プロペノエートの製造を例示するものである。
３−（３−ニトロフェノキシ）フェノール（１，７ｇ　
）と（Ｅ）−メチル２−（２−ブロムフェニル）−３−
メトキシプロペノエート（２，０ｇ、実施例１に記載し
た如く製造した）と炭酸カリウム（１，０ｇ）と塩化銅
（１）（１，０ｇ）との混合物を１７０〜１８０℃で５
時間攪拌し、次いで放冷した。該混合物を水で希釈し、
エーテルで抽出した。抽出液を水酸化ナトリウムの水溶
液及びブラインで連続的に洗浄し、次いで乾燥し、濃縮
させると褐色油（３，１２ｇ）を得た。溶離液としてヘ
キサン中に種々の割合（２０％まで）のエーテルを用い
てクロマトグラフィーにかけると黄色油として標記化合
物（１，０６ｇ、　３４％の収率）を得た。
’Ｈｎ、ｍ、ｒ、　（２７０ＭＨｚ）δ：３．６０（３
）１．　ｓ）、　３．７６（３Ｈ，ｓ）。
６．６６−６．８３（３８，ｍ）、　７．０２（ＬＨ，
ｄ）。
７．１８（ＩＨ，ｄ）、　７．２２−７．３８（３Ｈ，
ｍ）。
７．４５−７．５２（ＬＨ，ｍ）、　７．４９（ＬＨ，
ｓ）。
７．７８（ＬＨ，ｍ）、　７．９２−７．９７（ＩＨ，
ｍ）ｐｐｍ。

Claims (1)

  1. 【特許請求の範囲】 １、次式（II）： ▲数式、化学式、表等があります▼（II） （式中Ｘはハロゲンである）の化合物を塩基の存在下に
    次式（III）： ▲数式、化学式、表等があります▼（III） のフェノール又はフェノール（III）の塩と、好ましく
    は適当な遷移金属、遷移金属塩又は化合物又はこれの混
    合物よりなる触媒の存在下で反応させることからなる次
    式（ I ）： ▲数式、化学式、表等があります▼（ I ） （式中ベンゼン環Ｍ及びＮは場合によっては、本性の条
    件下で反応性でない置換基の１個又はそれ以上を担持す
    る）のプロペン酸化合物の製造方法。 ２、触媒量の銅金属又は銅塩又は化合物又はこれの混合
    物が存在している請求項１記載の方法。 ３、１００℃〜２００℃の温度で実施する請求項１又は
    ２記載の方法。 ４、塩基は無水の炭酸カリウムである請求項１〜３の何
    れかに記載の方法。
JP22481388A 1987-09-09 1988-09-09 プロペン酸誘導体の製造方法 Expired - Lifetime JP2780786B2 (ja)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB8721221 1987-09-09
GB878721221A GB8721221D0 (en) 1987-09-09 1987-09-09 Chemical process
GB878722537A GB8722537D0 (en) 1987-09-24 1987-09-24 Chemical process
GB8722537 1987-09-24
GB888804433A GB8804433D0 (en) 1988-02-25 1988-02-25 Chemical process
GB8804433 1988-02-25

Publications (2)

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JPH01125345A true JPH01125345A (ja) 1989-05-17
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EP (1) EP0307101B1 (ja)
JP (1) JP2780786B2 (ja)
AU (1) AU611935B2 (ja)
DE (1) DE3887603T2 (ja)
DK (1) DK498388A (ja)
ES (1) ES2061662T3 (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01121243A (ja) * 1987-09-09 1989-05-12 Imperial Chem Ind Plc <Ici> プロペン酸誘導体、それらの製造法及びそれらを含有する殺菌剤組成物
JPWO2005123859A1 (ja) * 2004-06-21 2008-04-10 リンテック株式会社 粘着シート
US7727615B2 (en) 2004-06-14 2010-06-01 Lintec Corporation Pressure-sensitive adhesive sheet
US8101884B2 (en) 2002-12-27 2012-01-24 Lintec Corporation Method for production of a pressure-sensitive adhesive sheet

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8811435D0 (en) * 1988-05-13 1988-06-15 Ici Plc Fungicides
GB8926630D0 (en) * 1989-11-24 1990-01-17 Ici Plc Fungicides

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01121243A (ja) * 1987-09-09 1989-05-12 Imperial Chem Ind Plc <Ici> プロペン酸誘導体、それらの製造法及びそれらを含有する殺菌剤組成物

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JPS5714554A (en) * 1980-06-27 1982-01-25 Ihara Chem Ind Co Ltd Production of 2-(substituted phenoxy)phenylacetic acid
GB2093021B (en) * 1981-01-24 1985-10-02 Reckitt & Colman Product Ltd 2-(2,4-dichlorophenoxy) phenylacetic acid
NZ213630A (en) * 1984-10-19 1990-02-26 Ici Plc Acrylic acid derivatives and fungicidal compositions
DE3519282A1 (de) * 1985-05-30 1986-12-04 Basf Ag, 6700 Ludwigshafen Acrylsaeureester und fungizide, die diese verbindungen enthalten
EP0472224B1 (en) * 1987-02-09 1994-04-27 Zeneca Limited Fungicides
GB8711538D0 (en) * 1987-05-15 1987-06-17 Ici Plc Fungicides
CH689350A5 (fr) * 1993-08-24 1999-03-15 Rollomatic Sa Machine à meuler.
JPH0775947A (ja) * 1993-09-07 1995-03-20 Mitsubishi Materials Corp スローアウェイチップの研削方法および装置

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01121243A (ja) * 1987-09-09 1989-05-12 Imperial Chem Ind Plc <Ici> プロペン酸誘導体、それらの製造法及びそれらを含有する殺菌剤組成物

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01121243A (ja) * 1987-09-09 1989-05-12 Imperial Chem Ind Plc <Ici> プロペン酸誘導体、それらの製造法及びそれらを含有する殺菌剤組成物
US8101884B2 (en) 2002-12-27 2012-01-24 Lintec Corporation Method for production of a pressure-sensitive adhesive sheet
JP4898221B2 (ja) * 2002-12-27 2012-03-14 リンテック株式会社 粘着シートおよびその製造方法
US7727615B2 (en) 2004-06-14 2010-06-01 Lintec Corporation Pressure-sensitive adhesive sheet
JPWO2005123859A1 (ja) * 2004-06-21 2008-04-10 リンテック株式会社 粘着シート

Also Published As

Publication number Publication date
DE3887603T2 (de) 1994-05-26
DK498388A (da) 1989-03-10
EP0307101A3 (en) 1991-04-10
US4937374A (en) 1990-06-26
AU611935B2 (en) 1991-06-27
EP0307101B1 (en) 1994-02-02
AU2166788A (en) 1989-03-09
DK498388D0 (da) 1988-09-07
JP2780786B2 (ja) 1998-07-30
ES2061662T3 (es) 1994-12-16
EP0307101A2 (en) 1989-03-15
DE3887603D1 (de) 1994-03-17

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