Methanol → Methyl 4-sulfanylbenzoate

HRID 265436Notes

Reaction equation

HRID 265436 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-sulfanylbenzoate

Procedure

To a solution of 4-mercaptobenzoic acid (Apin, 1.72 g, 11.17 mmol) in anhydrous methyl alcohol (20.0 mL) was added concentrated sulfuric acid (0.43 mL). The reaction mixture is then warmed to reflux for 16 h, concentrated in vacuo, diluted with ethyl acetate (100 mL) and washed with saturated sodium bicarbonate (2×100 mL). The organic phase is then separated, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 712 mg (Y: 38%) of the title product; 1H-NMR (CDCl3): δ 7.89 (d, J=8.7 Hz, 2H), 7.29 (d, J=8.7 Hz, 2H), 3.90 (s, 3H), 3.60 (s, 1H).

Workup

  1. temperatureThe reaction mixture is then warmed
  2. temperatureto reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. additiondiluted with ethyl acetate (100 mL)
  5. washwashed with saturated sodium bicarbonate (2×100 mL)
  6. customThe organic phase is then separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e50a276094814008b88cda2fade347e6
Source dataset
uspto-grants-1997_07
Patent number
US05648385

Reaction notes

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