Methanol → Methyl 3-mercaptobenzoate

HRID 926992Notes

Reaction equation

HRID 926992 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:16]O>>[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 95737Benzoic acid, 3-mercapto-

Product 1

HCID 4362804Methyl 3-mercaptobenzoate

Procedure

3-Mercaptobenzoic acid (10.0 g) was suspended in methanol (310 mL), added with sulfuric acid (0.3 mL), and stirred for 24 hours under reflux with heating. After cooling to room temperature, the solvent was evaporated under reduced pressure and water was added to residues. After adjusting to pH 8 by using a saturated aqueous solution of sodium hydrogen carbonate, it was extracted with ethyl acetate and dried over anhydrous sodium sulfate. After distilling the solvent under reduced pressure, the residues were purified by silica gel column chromatography (10% ethyl acetate/hexane) to obtain the title compound as a colorless oil.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. customthe solvent was evaporated under reduced pressure and water
  4. additionwas added to residues
  5. extractionwas extracted with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling the solvent under reduced pressure
  8. customthe residues were purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d4eddd5c1bc84e07b6e8023fe63ae745
Source dataset
uspto-grants-2016_03
Patent number
US09290440B2

Reaction notes

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