Benzyl mercaptan → 3-(Benzylsulfanyl)-3-methylbutanoic acid

HRID 326924Notes

Reaction equation

HRID 326924 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([OH:6])=[O:5].[CH2:8]([SH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1CCCCC1>[CH2:8]([S:15][C:2]([CH3:7])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7509Benzyl mercaptanHCID 109313-Methyl-2-butenoic acid

Product 1

HCID 149699823-(Benzylsulfanyl)-3-methylbutanoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

A solution of 3,3-dimethylacrylic acid (7 g, 70 mmol) and benzyl mercaptan (8.9 mL, 7.5 mmol) in piperidine (70 mL) was heated to reflux for 2 days. Piperidine was then evaporated and the product was partitioned between EtOAc and an aqueous solution of 1N HCl. The organic phases were washed with brine and dried over MgSO4. After evaporation of the solvent the product was distilled with a Kugelrohr apparatus under high vacuum (1 mmHg) to give 15.5 g with 99% yield.

Workup

  1. temperatureto reflux for 2 days
  2. customPiperidine was then evaporated
  3. customthe product was partitioned between EtOAc
  4. washThe organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvent the product
  7. distillationwas distilled with a Kugelrohr apparatus under high vacuum (1 mmHg)
  8. customto give 15.5 g with 99% yield

Sources & evidence

ORD record
ord-61b232decf3740a1a39d49166176f0cc
Source dataset
uspto-grants-1993_12
Patent number
US05270324

Reaction notes

Loading…