Benzyl mercaptan → 2-Benzylsulfanylmethylacrylic acid

HRID 1830131Notes

Reaction equation

HRID 1830131 reaction equation
Br[CH2:2][C:3](=[CH2:7])[C:4]([OH:6])=[O:5].[CH2:8]([SH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>CO>[CH2:8]([S:15][CH2:2][C:3](=[CH2:7])[C:4]([OH:6])=[O:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 5588842-(Bromomethyl)propenoic acid

Product 1

HCID 220539822-Benzylsulfanylmethylacrylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromomethylacrylic acid (3.00 g, 18.1 mmol) was dissolved in methanol (100 mL), cooled on an ice bath and treated with benzyl mercaptan. Aqueous sodium hydroxide (1N, 39.8 mL) was added dropwise and the reaction mixture was allowed to adjust to room temperature with stirring for 23 hours. Methanol was removed by rotary evaporation at reduced pressure and water (100 ml) was added to the residue, which was then washed with ether. The aqueous layer was cooled on ice and acidified to pH 2.5. The precipitated solid was isolated by filtration and dried to give 2-benzylsulfanylmethyl-acrylic acid (3.346 g, 89%).

Workup

  1. temperaturecooled on an ice bath
  2. customto adjust to room temperature
  3. customMethanol was removed by rotary evaporation at reduced pressure and water (100 ml)
  4. additionwas added to the residue, which
  5. washwas then washed with ether
  6. temperatureThe aqueous layer was cooled on ice
  7. customThe precipitated solid was isolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-91b31229acbe4780b89b453e36db7867
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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