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

HRID 342004Notes

Reaction equation

HRID 342004 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-196f747439e44c4d883fa5711beeb2e1
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Reaction notes

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