Methanol → Methyl 2-(3-mercaptophenyl)acetate

HRID 2108724Notes

Reaction equation

HRID 2108724 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:17]O>>[SH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:17])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 35431562-(3-Mercaptophenyl)acetic acid

Product 1

HCID 14820216Methyl 2-(3-mercaptophenyl)acetateYield 50%

Procedure

2-(3-mercaptophenyl)acetic acid (1.0 g, 6.0 mmol) was dissolved in dry methanol (40 mL). To this solution 10 drops concentrated sulfuric acid was added and the reaction mixture was heated to reflux for 36 hours. The reaction mixture was then concentrated to about half the volume, diluted with ethyl acetate, and the organic layer washed with saturated sodium bicarbonate solution, then dried over sodium sulfate and concentrated to an oil, 0.55 g, 3.0 mmol, 50% yield. 1H NMR 500 MHz (CDCl3) 7.05 ppm, 3H, m; 6.88 ppm, 1H, m; 3.53 ppm, 3H, s; 3.38 ppm, 2H, s.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 36 hours
  3. concentrationThe reaction mixture was then concentrated to about half the volume
  4. additiondiluted with ethyl acetate
  5. washthe organic layer washed with saturated sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to an oil, 0.55 g, 3.0 mmol, 50% yield

Sources & evidence

ORD record
ord-5a6a2816391a4ede9c71471a028e0e54
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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