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

HRID 258487Notes

Reaction equation

HRID 258487 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 921.3%

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 phase was 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 of the title compound (99% yield).

Workup

  1. temperatureto reflux for 2 days
  2. customPiperidine was then evaporated
  3. customthe product was partitioned between EtOAc
  4. washThe organic phase was 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)

Sources & evidence

ORD record
ord-0ceaaf20e0444672932e2c1062908d20
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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