Thioglycolic Acid → 4-(Carboxymethylthio)-3-oxobutanoic acid

HRID 557110

Reaction equation

HRID 557110 reaction equation
[SH:1][CH2:2][C:3]([OH:5])=[O:4].Cl[CH2:7][C:8](=[O:13])[CH2:9][C:10]([OH:12])=[O:11]>CO>[C:3]([CH2:2][S:1][CH2:7][C:8](=[O:13])[CH2:9][C:10]([OH:12])=[O:11])([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 1133Thioglycolic AcidHCID 119720Butanoic acid, 4-chloro-3-oxo-

Product 1

HCID 574805774-(Carboxymethylthio)-3-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23.5 °C

Procedure

To a round bottom flask containing mercaptoacetic acid (0.1 mol) dissolved in methanol (25 mL) is added 4-chloro-3-oxobutanoic acid (0.1 mol). The resulting mixture is heated at reflux temperature for about 2 hours. When the reaction is complete, the mixture is allowed to cool to room temperature (22-25° C.). Volatiles are removed under vacuum and the resulting residue is purified by column chromatography to yield 4-(carboxymethylthio)-3-oxobutanoic acid.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux temperature for about 2 hours
  3. customVolatiles are removed under vacuum
  4. customthe resulting residue is purified by column chromatography

Sources & evidence

ORD record
ord-cdc3abd1d7a244a59e3873e929f9236c
Source dataset
uspto-grants-2011_11
Patent number
US08058313B2

Linked notes

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