Carbon Dioxide → 5-Methyl-2-[(phenylmethyl)thio]benzoic acid

HRID 1076144Notes

Reaction equation

HRID 1076144 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([SH:17])=[C:12]([CH:16]=1)[C:13]([OH:15])=[O:14].[CH2:18](Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)=O>C(O)C.O>[CH2:18]([S:17][C:11]1[CH:10]=[CH:9][C:8]([CH3:7])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 15557788HCID 15557788, compound

Product 1

HCID 215422905-Methyl-2-[(phenylmethyl)thio]benzoic acidYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.15 g. (0.030 moles) of potassium carbonate in 50 ml. of water is successively added 100 ml. of ethanol, 5.05 g. (0.030 moles) of 5-methyl-2-mercaptobenzoic acid, and 3.8 g. (0.030 moles) of benzyl chloride. After the evolution of carbon dioxide ceases (about 10 minutes), the mixture is refluxed on a steam bath for one hour. The mixture is cooled, and the major portion of the solvent is evaporated under reduced pressure. The cloudy, white liquid residue is diluted to a volume of about 600 ml. with water. The mixture is filtered, cooled, and acidified with 6 N hydrochloric acid. The white precipitate which forms is separated, filtered, and triturated with about 400 ml. of water. Filtration and drying under high vacuum provides 6.9 g. (89 percent yield) of 2-benzylthio-5-methylbenzoic acid, m.p. 169°-171°C. sint. 167°C.

Workup

  1. temperatureThe mixture is cooled
  2. customthe major portion of the solvent is evaporated under reduced pressure
  3. additionThe cloudy, white liquid residue is diluted to a volume of about 600 ml
  4. filtrationThe mixture is filtered
  5. temperaturecooled
  6. customThe white precipitate which forms is separated
  7. filtrationfiltered
  8. customtriturated with about 400 ml
  9. filtrationFiltration
  10. customdrying under high vacuum
  11. customprovides 6.9 g

Sources & evidence

ORD record
ord-ec060f16a7044ae3b58133b00c951f64
Source dataset
uspto-grants-1976_05
Patent number
US03954994

Reaction notes

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