Methanol → Benzoic acid, 2-mercapto-, methyl ester

HRID 1910434Notes

Reaction equation

HRID 1910434 reaction equation
S(=O)(=O)(O)O.[SH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:16]O>>[SH:6][C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:16])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 54432-Mercaptobenzoic Acid

Product 1

HCID 21009Benzoic acid, 2-mercapto-, methyl esterYield 90%

Procedure

To a cooled solution of concentrated sulfuric acid (72 g) in methanol (1.5 L) at 0° C., was added 2-sulfanylbenzoic acid (300 g, 1.95 mol) in portions under argon atmosphere. After being refluxed with stirring for 18 hours, the reaction mixture was concentrated in vacuo. The residue was diluted with water (800 mL), basified with a saturated aqueous solution of sodium bicarbonate to about pH 7, and extracted with dichloromethane (600 mL×3). The combined organic layers were washed with brine (800 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford 300 g of methyl 2-sulfanylbenzoate (yield was 90%) as a light yellow oil, which was used for the next step without further purification.

Workup

  1. temperatureAfter being refluxed
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionThe residue was diluted with water (800 mL)
  4. extractionextracted with dichloromethane (600 mL×3)
  5. washThe combined organic layers were washed with brine (800 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b7b1c04bc294b52b1774c17f61084b0
Source dataset
uspto-grants-2013_12
Patent number
US08604019B2

Reaction notes

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