Methanol → Methyl 4-sulfanylbenzoate

HRID 1851678Notes

Reaction equation

HRID 1851678 reaction equation
[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH3:11]O>OS(O)(=O)=O.C(Cl)(Cl)Cl>[SH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:11])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 887Methanol2×HCID 957384-Mercaptobenzoic acid

Product 1

HCID 237573Methyl 4-sulfanylbenzoateYield 97.7%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of 4-mercapto benzoic acid (5 g, 32.4 mmol) in methanol (25 mL) was added catalytic H2SO4 (1-2 drops) and refluxed for 5-6 h. TLC (mobile phase-10% methanol in chloroform Rf. S.M.—0.2, product—0.6) shows absence of starting material and formation of product; the methanol was distilled off in vacuo and the residue was diluted with ethyl acetate. The organic layer was washed with water (2×25 mL) followed by 10% aq. sodium bicarbonate solution. The organic layer was dried over Na2SO4 and concentrated in vacuo to obtained the product as an off-white solid (Yield-5 g).

Workup

  1. temperaturerefluxed for 5-6 h
  2. distillationthe methanol was distilled off in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washThe organic layer was washed with water (2×25 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8754520c2656487daa44e56c3ec6d8f8
Source dataset
uspto-grants-2015_02
Patent number
US08957216B2

Reaction notes

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