Hydrochloric Acid → [(2-Chloro-3-methoxy-3-oxopropyl)sulfanyl]acetic acid

HRID 1248268Notes

Reaction equation

HRID 1248268 reaction equation
[OH-].[Na+].[SH:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:8][O:9][C:10](=[O:14])[C:11]([Cl:13])=[CH2:12].Cl>O>[CH3:8][O:9][C:10](=[O:14])[CH:11]([Cl:13])[CH2:12][S:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 6659Methyl 2-chloroacrylateHCID 14798Sodium Hydroxide

Product 1

HCID 14189835[(2-Chloro-3-methoxy-3-oxopropyl)sulfanyl]acetic acidYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under stirring there were added 0.063 gram (1.58 mmoles) of sodium hydroxide in 0.32 ml water to 1.00 gram (10.9 mmoles) of mercaptoacetic acid and 1.31 grams (10.9 mmoles) of 2-chloroacrylic acid methyl ester. Stirring was carried out subsequently for 24 hours at 10° C. After acidification of the reaction mixture with dilute hydrochloric acid the working up was carried out by extracting three times with diethyl ether, drying the combined ether phases with water free sodium sulfate and removal of the ether. There were obtained 2.00 grams (86% of theory) of 2-chloro-3-carboxymethylmercapto-propionic acid methyl ester as a colorless viscous oil.

Workup

  1. stirringStirring
  2. extractionby extracting three times with diethyl ether
  3. dry with materialdrying the combined ether phases
  4. customwith water free sodium sulfate and removal of the ether

Sources & evidence

ORD record
ord-00e4e72d142d4ef298a1409a4e471223
Source dataset
uspto-grants-1985_06
Patent number
US04523012

Reaction notes

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