Methanol → Methyl 2-(4-(methylsulfonyl)phenyl)acetate

HRID 1430643Notes

Reaction equation

HRID 1430643 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].S(=O)(=O)(O)O.[CH3:20]O>>[CH3:20][O:13][C:12](=[O:14])[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 5723454-Mesylphenylacetic acid

Product 1

HCID 16640928Methyl 2-(4-(methylsulfonyl)phenyl)acetateYield 99%

Procedure

A solution of (4-Methanesulfonyl-phenyl)-acetic acid (25 g, 116.69 mmol) in methanol (300 ml) is treated with catalytic amount of sulfuric acid (2 ml). The reaction mixture was refluxed for 24 h. The solvent was then removed under reduced pressure, residue was dissolve in ethyl acetate (200 ml), the organic layer washed with water (2×100 ml), brine (100 ml), dried over sodium sulfate, and solvent was removed under reduced pressure to give (4-Methanesulfonyl-phenyl)-acetic acid methyl ester 26.37 g, 99%). 1H NMR (400 MHz, CDCl3): δ 3.06 (s, 3H), 3.73 (s, 3H), 7.50 (d, J=8.4 Hz, 2H), 7.91 (d, J=8.4 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. customThe solvent was then removed under reduced pressure, residue
  3. dissolutionwas dissolve in ethyl acetate (200 ml)
  4. washthe organic layer washed with water (2×100 ml), brine (100 ml)
  5. dry with materialdried over sodium sulfate, and solvent
  6. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-b7b37fb6b114457c83cad0673f954a0c
Source dataset
uspto-grants-2015_01
Patent number
US08940900B2

Reaction notes

Loading…