Methyl 2-chloroacrylate → Methyl 2-chloro-3-[(2-methoxy-2-oxoethyl)sulfanyl]propanoate

HRID 1248267Notes

Reaction equation

HRID 1248267 reaction equation
[Na].[CH3:2][O:3][C:4](=[O:7])[CH2:5][SH:6].[CH3:8][O:9][C:10](=[O:14])[C:11]([Cl:13])=[CH2:12]>O>[CH3:8][O:9][C:10](=[O:14])[CH:11]([Cl:13])[CH2:12][S:6][CH2:5][C:4]([O:3][CH3:2])=[O:7]

Participants

5

Reactant 3

HCID 6659Methyl 2-chloroacrylateHCID 16907Methyl ThioglycolateHCID 5360545Sodium

Product 1

HCID 14189836Methyl 2-chloro-3-[(2-methoxy-2-oxoethyl)sulfanyl]propanoateYield 99.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.076 gram (3.31 mmoles) of metallic sodium were dissolved in 17.97 grams (169 mmoles) of thioglycolic acid methyl ester. This solution was then subsequently under stirring dropped into 20.0 grams (166 mmoles) of freshly distilled 2-chloro-acrylic acid methyl ester dissolved in 30 ml of water free methylene chloride within 1 hour at 25° C. After 4 hours post reaction at 25° C. it was worked up according to Example 1. There were obtained 37.5 grams (99.6% of theory) of 2-chloro-3-methoxycarbonylmethylmercapto-propionic acid methyl ester as a yellowish oil.

Workup

  1. customAfter 4 hours post reaction at 25° C. it

Sources & evidence

ORD record
ord-625a47066c594b0cbf9d5d8aa7352e32
Source dataset
uspto-grants-1985_06
Patent number
US04523012

Reaction notes

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