JPH02104560A - Production of optically active 2-chloropropionic acid ester - Google Patents
Production of optically active 2-chloropropionic acid esterInfo
- Publication number
- JPH02104560A JPH02104560A JP63256689A JP25668988A JPH02104560A JP H02104560 A JPH02104560 A JP H02104560A JP 63256689 A JP63256689 A JP 63256689A JP 25668988 A JP25668988 A JP 25668988A JP H02104560 A JPH02104560 A JP H02104560A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- acid ester
- formula
- distillation
- water
- 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.)
- Pending
Links
- -1 2-chloropropionic acid ester Chemical class 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000004821 distillation Methods 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000003287 optical effect Effects 0.000 claims abstract description 16
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- VIRPUNZTLGQDDV-UHFFFAOYSA-N chloro propanoate Chemical compound CCC(=O)OCl VIRPUNZTLGQDDV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 4
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical class OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000003905 agrochemical Substances 0.000 abstract 2
- 239000008346 aqueous phase Substances 0.000 abstract 2
- 239000012074 organic phase Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 description 9
- 150000007530 organic bases Chemical class 0.000 description 9
- 230000006340 racemization Effects 0.000 description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000010410 layer Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 150000003903 lactic acid esters Chemical class 0.000 description 5
- 238000001577 simple distillation Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WCTKUENARPWTAY-UHFFFAOYSA-N ac1l9mss Chemical compound OS(Cl)=O WCTKUENARPWTAY-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- LPEKGGXMPWTOCB-GSVOUGTGSA-N methyl (R)-lactate Chemical compound COC(=O)[C@@H](C)O LPEKGGXMPWTOCB-GSVOUGTGSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は高い光学純度を有する光学活性２−クロルプロ
ピオン酸エステルを製造する方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing optically active 2-chloropropionic acid ester having high optical purity.
本発明の目的物である光学活性２−クロルプロピオン酸
エステルは、光学活性フェノキシプロピオン酸系農薬等
の重要な中間体である。Optically active 2-chloropropionic acid ester, which is the object of the present invention, is an important intermediate for optically active phenoxypropionic acid pesticides and the like.
従来光学活性２−クロルプロピオン酸エステルを製造す
る方法としては、光学活性乳酸エステルと塩化チオニル
とを反応させて光学活性乳酸エステルのクロルスルフィ
ネートを生成し、） 次に塩酸ピリジンの存在下で前の
反応で得られた光学活性乳酸エステルのクロルスルフィ
ネートを熱分解する方法が知られている。 （Ｃｈｅｍ
、Ｓｏｃ。Conventionally, the method for producing optically active 2-chloropropionic acid ester involves reacting optically active lactic acid ester with thionyl chloride to produce optically active lactic acid ester chlorosulfinate, and then reacting it in the presence of pyridine hydrochloride. A method is known in which the optically active lactic acid ester chlorsulfinate obtained in the previous reaction is thermally decomposed. (Chem
, Soc.
Ｔｒａｎｓ、１０５ 、１１０３〜１１１５参照、）こ
の方法は塩酸ピリジンの使用量が多く、部分ラセミ化が
起こりやすく、又過剰の塩化チオニルを必要とする等の
欠点があった。Trans., 105, 1103-1115) This method had drawbacks such as the use of a large amount of pyridine hydrochloride, the tendency to cause partial racemization, and the need for an excessive amount of thionyl chloride.
これらの欠点を改善する方法として特開昭５６−７７４
３には、まず低温でピリジン等の有機塩基の存在下、光
学活性乳酸エステルと塩化チオニルを反応させ、続いて
徐々に加熱して温度を上昇させて光学活性乳酸エステル
のクロルスルフィネートを分解して光学活性２−クロル
プロピオン酸エステルを得るという方法が記載されてい
る。As a method to improve these drawbacks, Japanese Patent Application Laid-Open No. 56-774
Step 3 involves first reacting an optically active lactic acid ester with thionyl chloride in the presence of an organic base such as pyridine at low temperature, and then gradually increasing the temperature by heating to decompose the chlorosulfinate of the optically active lactic acid ester. A method for obtaining an optically active 2-chloropropionic acid ester is described.
しかしながら本発明者が追試したところ、反応粗製物を
蒸留して精製した光学活性２−クロルプロピオン酸エス
テルを得る工程が、蒸留時間が長くなると得られる２−
クロルプロピオン酸エステルの光学純度が低下するとい
う欠点があることがわかった。即ちフラスコスケールで
は短時間で蒸留を終えることは可能であるが、工業的規
模ではフラスコスケール並の時間で蒸留を終えることは
不可能であり、実用上問題があった。However, as a result of additional experiments conducted by the present inventors, it was found that the step of distilling the reaction crude product to obtain purified optically active 2-chloropropionate ester was difficult to obtain when the distillation time was prolonged.
It has been found that there is a drawback that the optical purity of chloropropionate ester is reduced. That is, although it is possible to complete distillation in a short time on a flask scale, on an industrial scale it is impossible to complete distillation in a time comparable to that on a flask scale, which poses a practical problem.
精製蒸留中に部分的にラセミ化が起こって得られる２−
クロルプロピオン酸エステルの光学純度が低下する原因
として、分解触媒として添加したピリジン等の有機塩基
がラセミ化触媒としても作用することが考えられる。又
精製蒸留中のラセミ化を抑制する方法として特開昭６１
−２７１２４９には硫酸等の不揮発性強酸の存在下で精
製蒸留する方法が記載されている。2- obtained by partial racemization during purification distillation
A possible cause of the decrease in optical purity of chloropropionate is that an organic base such as pyridine added as a decomposition catalyst also acts as a racemization catalyst. In addition, as a method for suppressing racemization during purification distillation, JP-A-61
-271249 describes a method of purification distillation in the presence of a nonvolatile strong acid such as sulfuric acid.
この方法ではラセミ化が抑制され、高い光学純度の目的
物が得られるものの、蒸留残渣として、硫酸の作用で生
成したと考えられるタール状物や、ピリジン等の有機塩
基の硫酸塩と考えられる固型物が残り、容器からの取出
し及び洗浄の作業が煩雑であるという問題があった。Although this method suppresses racemization and yields the target product with high optical purity, the distillation residue contains tar-like substances thought to have been produced by the action of sulfuric acid and solids thought to be sulfates of organic bases such as pyridine. There was a problem in that molds remained, making removal from the container and cleaning operations complicated.
本発明者はこれらの欠点を改善すべく鋭意検討を重ねた
結果、ピリジン等の有機塩基の存在下光学活性乳酸エス
テルのクロルスルフィネートを分解して得られる粗製光
学活性２−クロルプロピオン酸エステルを先ず水洗浄し
、次で水層を分離し、有機層のみを蒸留することにより
ラセミ化が抑制できることを見い出し本発明に到達した
。As a result of intensive studies to improve these drawbacks, the present inventors have developed a crude optically active 2-chloropropionic acid ester obtained by decomposing chlorosulfinate of an optically active lactic acid ester in the presence of an organic base such as pyridine. The present invention was achieved by discovering that racemization can be suppressed by first washing with water, then separating the aqueous layer, and distilling only the organic layer.
即ち、本発明は、次の式（１）
（式中Ｒは炭素原子を１〜６個含むアルキル基を意味す
る。）
で示される光学活性２−クロルプロピオン酸エステルを
、次の式（ＩＩ）
（式中Ｒは式（Ｉ）におけると同じ意味をもつ、）で示
される光学活性２−クロルスルフィンオキシプロピオン
酸エステルの塩基性触媒の存在下に於ける分解反応によ
り製造するにあたり、分解終了後、反応粗液を水洗浄し
たのち、蒸留精製することを特徴とする、光学活性２−
クロルプロピオン酸エステルの製造方法である。That is, the present invention converts an optically active 2-chloropropionic acid ester represented by the following formula (1) (wherein R means an alkyl group containing 1 to 6 carbon atoms) into a compound represented by the following formula (II). ) (wherein R has the same meaning as in formula (I)) When producing by decomposition reaction of optically active 2-chlorosulfine oxypropionic acid ester in the presence of a basic catalyst, the decomposition is completed. After that, the reaction crude liquid is washed with water, and then purified by distillation.
This is a method for producing chloropropionate.
ピリジン等の有機塩基の存在下、上記式（ＩＩ）で示さ
れる光学活性乳酸エステルのクロルスルフィネートを分
解して得られる粗製光学活性２−クロルプロピオン酸エ
ステル中には、ＳＯｔ及びＨＣＩが存在していて塩基性
物質のラセミ化作用を抑制しているが、蒸留工程中にＳ
ｏ、、 ＨＣＩが系外に逃げて塩基性物質がラセミ化触
媒として作用し、後の留分になるほど光学純度が低下す
ると考えられる。従って蒸留前に塩基性物質を系外へと
り除けばラセミ化が抑制できるのではないかと考えられ
る。SOt and HCI are present in the crude optically active 2-chloropropionic acid ester obtained by decomposing the optically active lactic acid ester chlorosulfinate represented by the above formula (II) in the presence of an organic base such as pyridine. This suppresses the racemization effect of basic substances, but S
o. It is thought that HCI escapes from the system and the basic substance acts as a racemization catalyst, resulting in lower optical purity in later fractions. Therefore, it is thought that racemization can be suppressed by removing basic substances from the system before distillation.
本発明者はこれらの考えに基づいて検討を重ね、塩基性
物質を水で抽出してとり除くという本発明の方法に到達
した。The present inventor has conducted repeated studies based on these ideas, and has arrived at the method of the present invention in which basic substances are removed by extraction with water.
本発明者の検討によれば、上記の分解反応終了時点にお
いて、反応粗液中の塩基性物質はＳＯ□又はＨＣＩと塩
を形成しており、これが水層への分配率を大きくしてお
り、本発明の狙いである塩基性物質を系外へとり除くと
いう効果をより一層高くするものと推定される。According to the inventor's study, at the end of the above decomposition reaction, the basic substance in the reaction crude liquid forms a salt with SO□ or HCI, which increases the distribution ratio to the aqueous layer. It is estimated that this will further enhance the effect of removing basic substances from the system, which is the aim of the present invention.
本発明による方法では、有機塩基存在下での光学活性乳
酸エステルのクロルスルフィネートの分解反応終了後に
、反応粗液に水を加えて十分混合して水洗浄を行ない次
で分液して水層を除去してから、残液の精製蒸留を行う
。In the method of the present invention, after the decomposition reaction of optically active lactic acid ester chlorosulfinate in the presence of an organic base is completed, water is added to the crude reaction solution, thoroughly mixed, and washed with water. After removing the layers, the residual liquid is subjected to purification distillation.
水層を分離した残液である有機層には若干の水分が含ま
れており、この為に蒸留中に目的物の加水分解が起こり
、収率が低下する可能性がある。従って本発明の実施に
当っては有機層に無水Ｎａ５Ｏａ＋ Ｍｇ５Ｏｓ等の脱
水剤を入れて水分を除去してから、精製蒸留を行うのが
望ましい。The organic layer, which is the residual liquid after separating the aqueous layer, contains some water, which may cause hydrolysis of the target product during distillation, resulting in a decrease in yield. Therefore, in carrying out the present invention, it is desirable to add a dehydrating agent such as anhydrous Na5Oa+Mg5Os to the organic layer to remove water, and then perform purification distillation.
使用される水の量は特に限定されるものではないが、有
機塩基の量の２０〜１００重量倍程度使用するのが望ま
しい、使用する水の量が多すぎると、水層への２−クロ
ルプロピオン酸エステルの溶解ロスが多（なって不利で
ある。一方少なすぎる場合は有機塩基が十分除去できな
い。The amount of water used is not particularly limited, but it is desirable to use about 20 to 100 times the weight of the organic base.If the amount of water used is too large, 2-chloro Dissolution loss of the propionic acid ester is large (which is disadvantageous).On the other hand, if it is too small, the organic base cannot be removed sufficiently.
尚水層への目的物の溶解ロスを少なくする為、水洗浄の
ＦｉｔＮａｘＳＯ４，ＮａＣ１等の無機塩の水溶液を使
用することも可能である。In addition, in order to reduce the loss of dissolution of the target substance into the aqueous layer, it is also possible to use an aqueous solution of an inorganic salt such as FitNaxSO4 or NaCl, which is washed with water.
本発明によればピリジン等の有機塩基の存在下、光学活
性乳酸エステルのクロルスルフィネートを分解して得ら
れる粗製光学活性２−クロルプロピオン酸エステルを水
洗浄した後、精製蒸留を行なうことにより、光学純度を
ほぼ保持したままで工業的有利に２−クロルプロピオン
酸のエステルが得られる。According to the present invention, a crude optically active 2-chloropropionic acid ester obtained by decomposing an optically active lactic acid ester, chlorsulfinate, in the presence of an organic base such as pyridine is washed with water, and then subjected to purification distillation. , an ester of 2-chloropropionic acid can be obtained with industrial advantage while substantially retaining its optical purity.
以下、例を挙げて本発明の詳細な説明するが、本発明は
これらの例に限定されるものではない。Hereinafter, the present invention will be explained in detail by giving examples, but the present invention is not limited to these examples.
実施例１
塩化チオニル２００ ｇ （１，６５モル）をフラスコ
に仕込み、そこへＤ−乳酸メチル１６４ ｇ （１，５
８モル、光学純度： ９８．２％）を室温で撹拌しなが
ら滴下した。このようにして粗製Ｄ−２−クロルスルフ
ィンオキシプロピオン酸メチルを得た。Example 1 200 g (1.65 mol) of thionyl chloride was charged into a flask, and 164 g (1.5 mol) of methyl D-lactate was charged therein.
8 mol, optical purity: 98.2%) was added dropwise at room temperature with stirring. In this way, crude methyl D-2-chlorosulfineoxypropionate was obtained.
滴下漏斗と二酸化硫黄吸収の為のアルカリ吸収缶を備え
たフラスコにピリジンを２ｇ入れ、６５°Ｃに加熱し、
前述の粗製Ｄ−２−クロルスルフィンオキシプロピオン
酸メチルを約２時間かけて滴下した０滴下終了後２時間
、６５“Ｃに保ってから室温まで冷却した。2 g of pyridine was placed in a flask equipped with a dropping funnel and an alkali canister for absorbing sulfur dioxide, and heated to 65°C.
The aforementioned crude methyl D-2-chlorosulfineoxypropionate was added dropwise over about 2 hours. After the completion of the dropwise addition, the temperature was kept at 65"C for 2 hours, and then the mixture was cooled to room temperature.
こうして得られた粗製Ｌ−２−クロルプロピオン酸メチ
ルを分液漏斗に移し、水を５０ｇを入れて十分振盪した
後、水層を分離した。有機層は無水硫酸ナトリウムで処
理した後、８Ｑ ｔｏｒｒの減圧下で単蒸留を行なった
。約３０分かけて８２ｇのＬ−２−クロルプロピオン酸
メチルを留出させた後−旦単蒸留を中断した。１００℃
で１５Ｈｒ加熱後単蒸留を再開し、１０２ｇのＬ−２−
クロルプロピオン酸メチルを得た。Ｄ−乳酸メチル基準
の収率は９５％で、前半と後半の留分の光学純度は共に
９７．８％であった。１０ｇの蒸留残渣があったが、流
動性があり、容易に容器からとり出すことができた。The thus obtained crude methyl L-2-chloropropionate was transferred to a separatory funnel, 50 g of water was added thereto, and the mixture was thoroughly shaken, and then the aqueous layer was separated. The organic layer was treated with anhydrous sodium sulfate and then subjected to simple distillation under reduced pressure of 8Q torr. After distilling off 82 g of methyl L-2-chloropropionate over a period of about 30 minutes, the simple distillation was interrupted. 100℃
After heating for 15 hours, simple distillation was restarted, and 102 g of L-2-
Methyl chloropropionate was obtained. The yield based on methyl D-lactate was 95%, and the optical purity of both the first and second half fractions was 97.8%. There was 10 g of distillation residue, but it was fluid and could be easily taken out from the container.
比較例１
単蒸留を行なう前に粗製Ｌ−２−クロルプロピオン酸メ
チルを水洗しないで、ＨｘＳＯａを４ｇ添加したこと以
外は実施例１と同様の操作を行なった。前半の留分の光
学純度は９７．８％で後半の留分の光学純度は９７．４
％であった。結晶の混じった１７ｇの蒸留残渣があり、
水を入れて結晶を溶解して容器からとり出したが、まだ
容器にタール状物が残っていたのでメタノールを入れて
これを溶解し、容器からとり出した。Comparative Example 1 The same operation as in Example 1 was performed except that 4 g of HxSOa was added without washing the crude methyl L-2-chloropropionate with water before performing simple distillation. The optical purity of the first half fraction is 97.8% and the optical purity of the second half is 97.4.
%Met. There was 17g of distillation residue mixed with crystals.
Water was added to dissolve the crystals and the crystals were taken out of the container, but tar-like material still remained in the container, so methanol was added to dissolve it and the crystals were taken out of the container.
比較例２
単蒸留を行なう前に粗製Ｌ−２−クロルプロピオン酸メ
チルを水洗しないこと以外は実施例１と同様の操作を行
なった。前半の留分の光学純度は９６．７％で後半の留
分の光学純度は７５．０％であった。Comparative Example 2 The same operation as in Example 1 was performed except that the crude methyl L-2-chloropropionate was not washed with water before performing simple distillation. The optical purity of the first half fraction was 96.7%, and the optical purity of the second half fraction was 75.0%.
Claims (1)
る。） で示される光学活性２−クロルプロピオン酸エステルを
、次の式（II） ▲数式、化学式、表等があります▼（II） （式中Ｒは式（ I ）におけると同じ意味をもつ。）で
示される光学活性２−クロルスルフィンオキシプロピオ
ン酸エステルの塩基性触媒の存在下に於ける分解反応に
より製造するにあたり、分解終了後、反応粗液を水洗浄
したのち、蒸留精製することを特徴とする、光学活性２
−クロルプロピオン酸エステルの製造方法。[Claims] Optical activity represented by the following formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R means an alkyl group containing 1 to 6 carbon atoms.) 2-chloropropionic acid ester has the optical activity 2 shown by the following formula (II) ▲Mathematical formula, chemical formula, table, etc.▼(II) (In the formula, R has the same meaning as in formula (I).) - Optical activity 2, which is produced by decomposition reaction of chlorsulfine oxypropionate ester in the presence of a basic catalyst, and after completion of decomposition, the reaction crude liquid is washed with water and then purified by distillation.
- A method for producing chloropropionate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63256689A JPH02104560A (en) | 1988-10-12 | 1988-10-12 | Production of optically active 2-chloropropionic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63256689A JPH02104560A (en) | 1988-10-12 | 1988-10-12 | Production of optically active 2-chloropropionic acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02104560A true JPH02104560A (en) | 1990-04-17 |
Family
ID=17296110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63256689A Pending JPH02104560A (en) | 1988-10-12 | 1988-10-12 | Production of optically active 2-chloropropionic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02104560A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008515789A (en) * | 2004-10-04 | 2008-05-15 | ロディア・シミ | Stereoselective method for generating fluorinated chiral molecules |
-
1988
- 1988-10-12 JP JP63256689A patent/JPH02104560A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008515789A (en) * | 2004-10-04 | 2008-05-15 | ロディア・シミ | Stereoselective method for generating fluorinated chiral molecules |
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