JP2847813B2 - Method for producing 1-alkoxy-4- (substituted) benzyloxybenzenes - Google Patents
Method for producing 1-alkoxy-4- (substituted) benzyloxybenzenesInfo
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- JP2847813B2 JP2847813B2 JP27527189A JP27527189A JP2847813B2 JP 2847813 B2 JP2847813 B2 JP 2847813B2 JP 27527189 A JP27527189 A JP 27527189A JP 27527189 A JP27527189 A JP 27527189A JP 2847813 B2 JP2847813 B2 JP 2847813B2
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- substituted
- alkoxy
- benzyloxybenzenes
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Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は高感度感熱紙添加剤、医薬、農薬原料などと
して利用される1−アルコキシ−4−(置換)ベンジル
オキシベンゼン類の製造方法に関する。Description: TECHNICAL FIELD The present invention relates to a method for producing 1-alkoxy-4- (substituted) benzyloxybenzenes used as additives for high-sensitivity thermal paper, raw materials for pharmaceuticals and agricultural chemicals, and the like. .
従来、1−アルコキシ−4−(置換)ベンジルオキシ
ベンゼン類の製造方法として、メタノール・水混合溶液
中、塩基の存在下に、4−(4′−ハロゲノベンジルオ
キシ)フェノール に3−ハロゲノ−1−プロパノール(HOCH2CH2CH2X2)
を反応させて1−(3−ヒドロキシプロポキシ)−4−
(4′−ハロゲノベンジルオキシ)ベンゼン を製造する方法が特開昭55−40651号公報に開示されて
いる。しかしこの方法では、得られる1−アルコキシ−
4−(置換)ベンジルオキシベンゼン類の純度が低く、
収率が低いなどの問題点がある。Conventionally, as a method for producing 1-alkoxy-4- (substituted) benzyloxybenzenes, 4- (4′-halogenobenzyloxy) phenol is used in a mixed solution of methanol and water in the presence of a base. 3-halogeno-1-propanol (HOCH 2 CH 2 CH 2 X 2 )
To give 1- (3-hydroxypropoxy) -4-
(4'-halogenobenzyloxy) benzene Is disclosed in JP-A-55-40651. However, in this method, the resulting 1-alkoxy-
Low purity of 4- (substituted) benzyloxybenzenes,
There are problems such as a low yield.
本発明の目的は、上記のような問題点を解決するた
め、高収率で、しかも高純度の1−アルコキシ−4−
(置換)ベンジルオキシベンゼン類を製造する方法を提
案することにある。SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned problems by providing a high-yield and high-purity 1-alkoxy-4-
It is to propose a method for producing (substituted) benzyloxybenzenes.
本発明は、非プロトン性極性溶媒中、塩基の存在下
に、4−(置換)ベンジルオキシフェノール類とアルキ
ル化剤とを反応させることを特徴とする1−アルコキシ
−4−(置換)ベンジルオキシベンゼン類の製造方法で
ある。The present invention provides a method for reacting a 4- (substituted) benzyloxyphenol with an alkylating agent in an aprotic polar solvent in the presence of a base. This is a method for producing benzenes.
本発明では、「(置換)」という表記は置換基による
置換がある場合と、ない場合の両方を含むことを示して
いる。In the present invention, the notation “(substituted)” indicates that it includes both cases with and without substitution by a substituent.
本発明では出発原料となる4−(置換)ベンジルオキ
シフェノール類として、下記一般式〔I〕で表わされる
ものが使用できる。In the present invention, as the starting material, 4- (substituted) benzyloxyphenols represented by the following general formula [I] can be used.
(式中、R1は水素原子、ハロゲン原子または置換基を示
す。) 前記一般式〔I〕のR1のハロゲン原子としては、フッ
素、塩素、臭素、ヨウ素をあげることができる。 (In the formula, R 1 represents a hydrogen atom, a halogen atom or a substituent.) Examples of the halogen atom of R 1 in the general formula [I] include fluorine, chlorine, bromine and iodine.
前記一般式〔I〕のR1の置換基としては、例えばメチ
ル基、エチル基等のアルキル基;メトキシ基、エトキシ
基等のアルコキシ基;ニトロ基などをあげることができ
る。Examples of the substituent of R 1 in the general formula [I] include an alkyl group such as a methyl group and an ethyl group; an alkoxy group such as a methoxy group and an ethoxy group; and a nitro group.
前記一般式〔I〕で表わされる4−(置換)ベンジル
オキシフェノール類の具体的なものとしては、例えば4
−(4′−クロロベンジルオキシ)フェノール、4−ベ
ンジルオキシフェノール、4−(4′−メトキシベンジ
ルオキシ)フェノール、4−(4′−メチルベンジルオ
キシ)フェノール、4−(4′−ニトロベンジルオキ
シ)フェノールなどをあげることができる。Specific examples of 4- (substituted) benzyloxyphenols represented by the general formula [I] include, for example, 4
-(4'-chlorobenzyloxy) phenol, 4-benzyloxyphenol, 4- (4'-methoxybenzyloxy) phenol, 4- (4'-methylbenzyloxy) phenol, 4- (4'-nitrobenzyloxy) ) Phenol and the like.
前記一般式〔I〕で表わされる4−(置換)ベンジル
オキシフェノール類を製造するには公知の方法が採用で
き、例えば水酸化ナトリウムなどの塩基をメタノールな
どの溶媒に溶解し、次にこの溶液にヒドロキシノンおよ
び4−クロロベンジルクロリドなどのハロゲン化4−
(置換)ベンジルを加え、撹拌下に加熱還流することに
より4−(置換)ベンジルオキシフェノール類が製造さ
れる。反応終了後は不溶性物質を濾過などにより固液分
離した後、蒸留などの方法により溶媒を除去したものを
そのまま、またはさらにメタノール、アセトンなどと
水、トルエン、ヘキサンなどを用いて再結晶させたもの
を本発明の製造方法向け原料として使用できる。A known method can be employed for producing the 4- (substituted) benzyloxyphenol represented by the general formula [I]. For example, a base such as sodium hydroxide is dissolved in a solvent such as methanol, and then this solution is dissolved. And halogenated 4- such as hydroxynon and 4-chlorobenzyl chloride.
By adding (substituted) benzyl and heating to reflux with stirring, 4- (substituted) benzyloxyphenols are produced. After the completion of the reaction, the insoluble substance is separated into solid and liquid by filtration or the like, and then the solvent from which the solvent has been removed by distillation or the like, or recrystallized using methanol, acetone, etc. and water, toluene, hexane, etc. Can be used as a raw material for the production method of the present invention.
本発明ではアルキル化剤として、下記一般式〔II〕で
表わされるアルキル化剤が使用できる。In the present invention, an alkylating agent represented by the following general formula [II] can be used as the alkylating agent.
R2X …〔II〕 (式中、R2はアルキル基、Xはハロゲン原子、−OSO3R3
基または−OSO2Ar基を示す。ここでR3はアルキル基、Ar
は芳香族炭化水素基を示す。) 前記一般式〔II〕のR2のアルキル基としては、例えば
メチル基、エチル基、プロピル基等の炭素数1〜8のア
ルキル基;シクロヘキシル基等の炭素数6〜8のシクロ
アルキル基などをあげることができる。これらのアルキ
ル基は水酸基などの置換基で置換された置換アルキル基
であってもよく、また不飽和結合を持つアルキル基(た
だし、ビニル基、置換ビニル基は除く)であってもよ
い。R 2 X ... [II] (wherein, R 2 is an alkyl group, X is a halogen atom, -OSO 3 R 3
Group or —OSO 2 Ar group. Where R 3 is an alkyl group, Ar
Represents an aromatic hydrocarbon group. Examples of the alkyl group of R 2 in the general formula [II] include an alkyl group having 1 to 8 carbon atoms such as a methyl group, an ethyl group, and a propyl group; a cycloalkyl group having 6 to 8 carbon atoms such as a cyclohexyl group; Can be given. These alkyl groups may be substituted alkyl groups substituted with a substituent such as a hydroxyl group, or may be alkyl groups having an unsaturated bond (however, vinyl groups and substituted vinyl groups are excluded).
前記一般式〔II〕のXのハロゲン原子としては、塩
素、臭素、ヨウ素などをあげることができる。またR3と
してはメチル基、エチル基などのアルキル基をあげるこ
とができる。Arとしては 基などをあげることができる。Examples of the halogen atom of X in the general formula [II] include chlorine, bromine, and iodine. R 3 may be an alkyl group such as a methyl group and an ethyl group. As Ar Groups and the like.
前記一般式〔II〕で表わされるアルキル化剤の具体的
なものとしては、例えば塩化メチル、塩化エチル、塩化
プロピル、臭化メチル、臭化エチル、臭化プロピル、臭
化n−ブチル、ヨウ化メチル、ジメチル硫酸、ジエチル
硫酸、 HOCH2CH2CH2Clなどをあげることができる。Specific examples of the alkylating agent represented by the general formula [II] include, for example, methyl chloride, ethyl chloride, propyl chloride, methyl bromide, ethyl bromide, propyl bromide, n-butyl bromide, iodide Methyl, dimethyl sulfate, diethyl sulfate, HOCH 2 CH 2 CH 2 Cl and the like.
アルキル化剤はアルキル化剤/4−(置換)ベンジルオ
キシフェノール類のモル比で0.5〜5、好ましくは1〜
2の割合で使用するのが好ましい。The alkylating agent is used in a molar ratio of alkylating agent / 4- (substituted) benzyloxyphenols of 0.5 to 5, preferably 1 to 5.
It is preferred to use at a ratio of 2.
本発明で使用する非プロトン性極性溶媒としては、例
えばN,N−ジメチルアセトアミド、N,N−ジエチルアセト
アミド等のN,N−ジアルキルアセトアミド、N,N−ジメチ
ルホルムアミド、N−メチルピロリドン、N,N,N′,N′
−テトラメチル尿素、1,3−ジメチル−2−イミダゾリ
ジノン、ジメチルスルホキシド、スルホラン、ヘキサメ
チルリン酸トリアミドなどをあげることができる。Examples of the aprotic polar solvent used in the present invention include N, N-dimethylacetamide, N, N-dialkylacetamide such as N, N-diethylacetamide, N, N-dimethylformamide, N-methylpyrrolidone, N, N ', N'
-Tetramethylurea, 1,3-dimethyl-2-imidazolidinone, dimethylsulfoxide, sulfolane, hexamethylphosphoric triamide and the like.
非プロトン性極性溶媒は4−(置換)ベンジルオキシ
フェノール類1重量部に対して0.5〜15重量部、好まし
くは2〜8重量部の割合で使用するのが好ましい。The aprotic polar solvent is preferably used in an amount of 0.5 to 15 parts by weight, preferably 2 to 8 parts by weight, based on 1 part by weight of 4- (substituted) benzyloxyphenols.
本発明で使用する塩基としては、例えば水酸化ナトリ
ウム、水酸化カリウム等のアルカリ金属水酸化物;炭酸
ナトリウム、炭酸カリウム等のアルカリ金属炭素塩;水
酸化カルシウム、水酸化バリウム等のアルカリ土類金属
水酸化物;炭酸カルシウム、炭酸バリウム等のアルカリ
土類金属炭酸塩;炭酸水素ナトリウム、炭酸水素カリウ
ム等のアルカリ金属炭酸水素塩などをあげることができ
る。これらの中ではアルカリ金属水酸化物およびアルカ
リ金属炭酸塩が好ましく、特に水酸化ナトリウム、水酸
化カリウム、炭酸カリウムが好ましい。Examples of the base used in the present invention include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbon salts such as sodium carbonate and potassium carbonate; alkaline earth metals such as calcium hydroxide and barium hydroxide. Hydroxides; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; and alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate. Among these, alkali metal hydroxides and alkali metal carbonates are preferred, and sodium hydroxide, potassium hydroxide and potassium carbonate are particularly preferred.
塩基は固体のまま使用してもよいし、適当な溶媒に溶
解して溶液で使用してもよい。The base may be used as it is, or may be dissolved in an appropriate solvent and used in a solution.
塩基は塩基/4−(置換)ベンジルオキシフェノール類
のモル比で0.5〜5、好ましくは1〜2の割合で使用す
るのが好ましい。The base is preferably used in a molar ratio of base / 4- (substituted) benzyloxyphenols of 0.5 to 5, preferably 1 to 2.
本発明では4−(置換)ベンジルオキシフェノール類
として前記一般式〔I〕で表わされるものを、アルキル
化剤として前記一般式〔II〕で表わされるものを使用し
た場合、下記一般式〔III〕で表わされる1−アルコキ
シ−4−(置換)ベンジルオキシベンゼン類が製造され
る。In the present invention, when 4- (substituted) benzyloxyphenols represented by the general formula [I] are used and alkylating agents represented by the general formula [II] are used, the following general formula [III] 1-alkoxy-4- (substituted) benzyloxybenzenes represented by the formula are produced.
(式中、R1は前記一般式〔I〕のものと同じであり、R2
は前記一般式〔II〕のものと同じである。) 反応は非プロトン性極性溶媒中で、4−(置換)ベン
ジルオキシフェノール類と塩基とを反応させ、次にアル
キル化剤を供給して反応させる方法、4−(置換)ベン
ジルオキシフェノール類とアルキル化剤とを混合し、次
に塩基を供給して反応させる方法などが採用できる。 (In the formula, R 1 is the same as in the general formula (I), R 2
Is the same as that of the general formula [II]. The reaction is carried out by reacting 4- (substituted) benzyloxyphenols with a base in an aprotic polar solvent and then reacting by supplying an alkylating agent. A method in which an alkylating agent is mixed and then a base is supplied to cause a reaction can be employed.
反応条件は、反応温度が通常30〜150℃、好ましくは6
0〜100℃、反応圧力が通常1〜10気圧、好ましくは1〜
2気圧、反応時間が通常0.5〜12時間、好ましくは2〜
6時間の範囲で設定するのが適当である。The reaction conditions are such that the reaction temperature is usually 30 to 150 ° C, preferably 6
0 to 100 ° C, reaction pressure is usually 1 to 10 atm, preferably 1 to 10 atm
2 atm, reaction time is usually 0.5 to 12 hours, preferably 2 to
It is appropriate to set within the range of 6 hours.
反応を行うための反応器は特に限定されないが、槽型
が特に好ましい。反応方式も特に限定されず、バッチ
式、連続式などの方式により、スラリーまたは液相反応
として行うことができる。The reactor for carrying out the reaction is not particularly limited, but a tank type is particularly preferred. The reaction system is not particularly limited, and the reaction can be carried out as a slurry or liquid phase reaction by a system such as a batch system or a continuous system.
以上のような方法により、1−アルコキシ−4−(置
換)ベンジルオキシベンゼン類が反応系内の濃度として
10〜40重量%の濃度で製造できる。According to the method as described above, 1-alkoxy-4- (substituted) benzyloxybenzenes are used as the concentration in the reaction system.
It can be manufactured at a concentration of 10 to 40% by weight.
本発明の製造方法は、使用した原料のほとんどが1−
アルコキシ−4−(置換)ベンジルオキシベンゼン類に
変換されるので、反応終了後は濾過などにより固体を除
去した反応混合液に水などを加えて析出する結晶を濾過
するだけで高純度の1−アルコキシ−4−(置換)ベン
ジルオキシベンゼン類が高収率で得られる。従って反応
終了後の分離精製が極めて容易である。例えば、反応終
了後、反応混合物を中和した後、塩を濾別し、この反応
混合液を60℃程度に加熱し、これに水を滴下し、撹拌下
に常温まで冷却して結晶を析出させるなどの方法によ
り、収率90%以上で純度が通常99%以上の1−アルコキ
シ−4−(置換)ベンジルオキシベンゼン類が製造でき
る。In the production method of the present invention, most of the raw materials used are 1-
Since it is converted to alkoxy-4- (substituted) benzyloxybenzenes, after completion of the reaction, water and the like are added to the reaction mixture from which solids have been removed by filtration or the like, and only crystals that precipitate are filtered and filtered. Alkoxy-4- (substituted) benzyloxybenzenes are obtained in high yield. Therefore, separation and purification after the completion of the reaction are extremely easy. For example, after completion of the reaction, after neutralizing the reaction mixture, the salt is filtered off, the reaction mixture is heated to about 60 ° C., water is added dropwise thereto, and the mixture is cooled to room temperature with stirring to precipitate crystals. By such a method, 1-alkoxy-4- (substituted) benzyloxybenzenes having a yield of 90% or more and a purity of usually 99% or more can be produced.
このようにして得られた1−アルコキシ−4−(置
換)ベンジルオキシベンゼン類は高感度感熱紙添加剤、
医薬、農薬原料などとして利用できる。The thus obtained 1-alkoxy-4- (substituted) benzyloxybenzenes are highly sensitive thermal paper additives,
It can be used as a raw material for medicines and agricultural chemicals.
本発明によれば、非プロトン性極性溶媒中、塩基の存
在下に、4−(置換)ベンジルオキシフェノール類とア
ルキル化剤とを反応させて1−アルコキシ−4−(置
換)ベンジルオキシベンゼン類を製造するようにしたの
で、高収率で、しかも高純度の1−アルコキシ−4−
(置換)ベンジルオキシベンゼン類が製造できる。According to the present invention, 4- (substituted) benzyloxyphenols are reacted with an alkylating agent in an aprotic polar solvent in the presence of a base to form 1-alkoxy-4- (substituted) benzyloxybenzenes. To produce 1-alkoxy-4- with high yield and high purity.
(Substituted) benzyloxybenzenes can be produced.
〔実施例〕 次に本発明の実施例について説明する。Example Next, an example of the present invention will be described.
実施例1 撹拌機、温度計、冷却器および供給口を備え付けた30
0ml4つ口フラスコに4−(4′−クロロベンジルオキ
シ)フェノール(以下、CBPと略記する)23.5g(0.1モ
ル)およびN,N−ジメチルアセトアミド(以下、DMACと
略記する)80.0gを仕込み、反応系内を窒素置換したの
ち98%(固形)水酸化ナトリウム4.8g(0.12モル)を加
え、70℃で1時間撹拌した。次いで塩化エチル7.8g(0.
12モル)を70〜75℃で1時間かけて供給し、その後さら
に70℃で2時間加熱撹拌した。Example 1 30 equipped with a stirrer, thermometer, cooler and supply port
23.5 g (0.1 mol) of 4- (4'-chlorobenzyloxy) phenol (hereinafter abbreviated as CBP) and 80.0 g of N, N-dimethylacetamide (hereinafter abbreviated as DMAC) were charged into a 0 ml four-necked flask, After replacing the inside of the reaction system with nitrogen, 4.8 g (0.12 mol) of 98% (solid) sodium hydroxide was added, and the mixture was stirred at 70 ° C. for 1 hour. Then 7.8 g of ethyl chloride (0.
12 mol) at 70-75 ° C over 1 hour, and then heated and stirred at 70 ° C for 2 hours.
次に85%リン酸1.7gを加えて中和したのち反応混合物
を濾過し、塩をDMAC 10mlでリンスした。濾液とリンス
液を合わせて60℃に加熱し、これに水40mlを1時間かけ
て滴下し、撹拌下に室温まで冷却した。析出した結晶を
濾過し、水300mlでリンスしたのち減圧下に乾燥する
と、純度99.8%の1−エトキシ−4−(4′−クロロベ
ンジルオキシ)ベンゼン(以下、ECBBと略記する)が2
4.0g(収率91.4%)得られた。The reaction mixture was filtered after neutralization by adding 1.7 g of 85% phosphoric acid, and the salt was rinsed with 10 ml of DMAC. The filtrate and the rinsing solution were combined and heated to 60 ° C., to which 40 ml of water was added dropwise over 1 hour, and cooled to room temperature with stirring. The precipitated crystals were filtered, rinsed with 300 ml of water, and dried under reduced pressure to give 99.8% pure 1-ethoxy-4- (4'-chlorobenzyloxy) benzene (hereinafter abbreviated as ECBB).
4.0 g (91.4% yield) was obtained.
実施例2〜4 実施例1においてDMACの代りに第1表に示す溶媒を用
いた以外は実施例1と同様に行い、第1表に示す結果を
得た。Examples 2 to 4 The same procedures as in Example 1 were carried out except that the solvents shown in Table 1 were used instead of DMAC, and the results shown in Table 1 were obtained.
実施例5〜7 実施例1において塩化エチルの代りに第2表に示すア
ルキル化剤を第2表に示す量用いた以外は実施例1と同
様に行い、第2表に示す結果を得た。 Examples 5 to 7 The same procedure as in Example 1 was carried out except that the alkylating agent shown in Table 2 was used in place of ethyl chloride in the amount shown in Table 2, and the results shown in Table 2 were obtained. .
実施例8〜9 実施例1においてCBPの代りに第3表に示すフェノー
ル類を第3表に示す量用いた以外は実施例1と同様に行
い、第3表に示す結果を得た。 Examples 8 to 9 The same procedures as in Example 1 were carried out except that the phenols shown in Table 3 were used in place of CBP in the amounts shown in Table 3, and the results shown in Table 3 were obtained.
実施例10 撹拌機、温度計、冷却器および供給口を備え付けた30
0ml4つ口フラスコにCBP 23.5g(0.1モル)およびDMAC 6
0.0gを仕込み、反応系内を窒素置換したのち臭化n−ブ
チル13.7g(0.1モル)を加え、80℃に昇温したのち、炭
酸カリウム13.8g(0.1モル)を15分間隔で4回に分けて
加え、さらに80℃で5時間加熱撹拌した。反応混合物を
濾過し、塩をDMAC 20mlでリンスし、濾液とリンス液を
合わせて60℃に加熱し、これに水40mlを1時間かけて滴
下し、撹拌下に室温まで冷却した。析出した結晶を濾過
し、水200mlでリンスしたのち減圧下に乾燥すると、純
度99.8%の1−ブトキシ−4−(4′−クロロベンジル
オキシ)ベンゼンが26.5g(収率91.0%)得られた。 Example 10 30 equipped with a stirrer, thermometer, cooler and supply port
In a 0 ml four-necked flask, 23.5 g (0.1 mol) of CBP and DMAC 6
After charging 0.0 g, the inside of the reaction system was replaced with nitrogen, 13.7 g (0.1 mol) of n-butyl bromide was added, and the temperature was raised to 80 ° C., and 13.8 g (0.1 mol) of potassium carbonate was added 4 times at intervals of 15 minutes. And stirred under heating at 80 ° C. for 5 hours. The reaction mixture was filtered, the salt was rinsed with 20 ml of DMAC, the combined filtrate and rinse were heated to 60 ° C., to which 40 ml of water was added dropwise over 1 hour and cooled to room temperature with stirring. The precipitated crystals were filtered, rinsed with 200 ml of water, and dried under reduced pressure to obtain 26.5 g (91.0% yield) of 19.8% pure 1-butoxy-4- (4'-chlorobenzyloxy) benzene. .
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Claims (1)
に、4−(置換)ベンジルオキシフェノール類とアルキ
ル化剤とを反応させることを特徴とする1−アルコキシ
−4−(置換)ベンジルオキシベンゼン類の製造方法。1. A 1-alkoxy-4- (substituted) benzyl, which comprises reacting a 4- (substituted) benzyloxyphenol with an alkylating agent in an aprotic polar solvent in the presence of a base. A method for producing oxybenzenes.
Priority Applications (1)
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JP27527189A JP2847813B2 (en) | 1989-10-23 | 1989-10-23 | Method for producing 1-alkoxy-4- (substituted) benzyloxybenzenes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP27527189A JP2847813B2 (en) | 1989-10-23 | 1989-10-23 | Method for producing 1-alkoxy-4- (substituted) benzyloxybenzenes |
Publications (2)
Publication Number | Publication Date |
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JPH03135937A JPH03135937A (en) | 1991-06-10 |
JP2847813B2 true JP2847813B2 (en) | 1999-01-20 |
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JP27527189A Expired - Fee Related JP2847813B2 (en) | 1989-10-23 | 1989-10-23 | Method for producing 1-alkoxy-4- (substituted) benzyloxybenzenes |
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JP (1) | JP2847813B2 (en) |
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1989
- 1989-10-23 JP JP27527189A patent/JP2847813B2/en not_active Expired - Fee Related
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JPH03135937A (en) | 1991-06-10 |
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