ChemicalBook CAS DataBase List (S)-(-)-2-Chloropropionic acid

(S)-(-)-2-Chloropropionic acid synthesis

8synthesis methods

Product Name:(S)-(-)-2-Chloropropionic acid
CAS Number:29617-66-1
Molecular formula:C3H5ClO2
Molecular Weight:108.52

JP 061172846 provides a method for resolving racemic 2-chloropropionic acid using an optically active 2-aryl-2-isopropylethylamine as a resolving agent to obtain (S)-(-)-2-Chloropropionic acid (yield 24.2% and enantiomeric excess 83.2%). DE 4328231 provides a method for catalyzing the hydrolysis of 2-chloropropionic acid esters by a hydrolase (Pseudomonas Lipase) to hydrolyze (S)-2-chloropropionic acid esters to generate (S)-(-)-2-Chloropropionic acid.

56-41-7 Synthesis

56-41-7
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29617-66-1
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Yield:29617-66-1 94%

Reaction Conditions:

with hydrogenchloride;nitrosylchloride in water at 0; for 1 h;Temperature;

Steps:

3 Example 3
In a 500-ml three-necked flask (with a thermometer and stirrer), 8.9 g of L-alanine (0.1 mol) and 90.3 g of hydrochloric acid (mass fraction 20%) were added and dissolved by stirring to control the temperature at about 0°C.After introducing a mixed gas of nitrosyl chloride and hydrogen chloride, the conversion of the raw materials was completed, and the ventilation was stopped. The molar ratio of nitrosyl chloride to L-alanine was 1.5:1, and hydrogen chloride gas was introduced to saturate the hydrochloric acid.After stirring for 1 hour, 140 g of ammonia (20% by mass) was added in portions, followed by extraction with dichloromethane (50 ml*3), and the extracts were combined.After adding 5 g anhydrous calcium chloride to dry, it was filtered and distilled to obtain 10.2 g of L-2-chloropropionic acid (yield 94.0%, ee value 98.7%).

References:

Nanjing Hong Sun Biochemical Co., Ltd.;Ding Yongshan;Yuan Yi;Wang Fujun;Jiang Jianhua;Chen Xinchun CN107879925, 2018, A Location in patent:Paragraph 0021; 0023; 0025; 0027; 0029

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