Methacrylic Acid → 3-(Acetylthio)-2-methylpropanoic acid

HRID 1381066Notes

Reaction equation

HRID 1381066 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:7]([OH:10])(=[S:9])[CH3:8]>>[C:7]([S:9][CH2:3][CH:2]([CH3:4])[C:1]([OH:6])=[O:5])(=[O:10])[CH3:8]

Participants

3

Reactant 2

HCID 4093Methacrylic AcidHCID 178418634HCID 178418634, compound

Product 1

HCID 1180733-(Acetylthio)-2-methylpropanoic acidYield 70%

Conditions

Temperature
95 °C

Procedure

With stirring, 1 mol of methacrylic acid was added to 1.4 mol of fresh-distilled thioacetic acid being kept under N2 atmosphere. To the extent it was still necessary to do so in view of the heat liberated in course of the reaction, the reaction mixture was heated slowly to approximately 95° C. (reflux) and, subsequently, maintained at this temperature for 1 to 2 hours. After removing the excess thioacetic acid by distillation at atmospheric pressure, crude DL-S-acetyl-β-mercaptoisobutyric acid was obtained by the process of vacuum distillation (about 135° C. at 4 mm Hg). To purify this crude product, it was poured out in 200 ml of hexane and the product crystallized out was filtered off and dried in the air. The yield was 70%; melting point: about 39° C. (literature: 40°-40.5° C.; Chemical Abstracts 38, 3616).

Workup

  1. customliberated in course of the reaction
  2. temperature(reflux)
  3. temperaturesubsequently, maintained at this temperature for 1 to 2 hours
  4. customAfter removing the excess thioacetic acid
  5. distillationby distillation at atmospheric pressure

Sources & evidence

ORD record
ord-57ac98e805fc4724963cdbd6133f7405
Source dataset
uspto-grants-1986_04
Patent number
US04585595

Reaction notes

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