Methanol → Methyl 4-sulfanylbenzoate

HRID 131298

Reaction equation

HRID 131298 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 957384-Mercaptobenzoic acid

Product 1

HCID 237573Methyl 4-sulfanylbenzoateYield 99%

Procedure

To a solution of 4-mercaptobenzoic acid (1.5 g) in methanol (20 mL) is added conc. sulfuric acid (0.5 mL) and the mixture is refluxed under heating overnight. The reaction mixture is evaporated to remove solvent and the residue is neutralized with a saturated sodium hydrogencarbonate solution. The mixture is extracted with ethyl acetate and the extract is concentrated in vacuo to give methyl 4-mercaptobenzoate (1.6 g, yield; 99%) as a colorless oil. MS (APCI) m/z: 167 [M−H]−

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating overnight
  3. customThe reaction mixture is evaporated
  4. customto remove solvent
  5. extractionThe mixture is extracted with ethyl acetate
  6. concentrationthe extract is concentrated in vacuo

Sources & evidence

ORD record
ord-f51b70acb2e7448bbb18b4a5d91736aa
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Linked notes

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