Ethanol → Ethyl 4-(methylsulfonyl)phenylacetate

HRID 729694Notes

Reaction equation

HRID 729694 reaction equation
O=S(Cl)Cl.[CH3:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH3:19][CH2:20]O>>[CH2:19]([O:17][C:16](=[O:18])[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([S:6]([CH3:5])(=[O:7])=[O:8])=[CH:14][CH:13]=1)[CH3:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 5723454-Mesylphenylacetic acid

Product 1

HCID 12238955Ethyl 4-(methylsulfonyl)phenylacetate

Conditions

Temperature
20 °C

Procedure

SOCl2 (8.2 mL, 112.0 mmol) was added to a stirred suspension of (4-methanesulfonylphenyl)acetic acid (20.00 g, 93.3 mmol) in EtOH (80 mL) at −10° C. The mixture was allowed to warm up to 20° C. over 16 h, then the solvents were removed under reduced pressure. The remainder was dissolved in EtOAc, then the resulting solution was washed with H2O until the pH of the aqueous phase was neutral. The EtOAc solution was washed further with saturated aqueous Na2CO3, before being dried (MgSO4). Filtration and solvent evaporation furnished the title compound: m/z (ES+)=284.1 [M+MeCN+H]+.

Workup

  1. customthe solvents were removed under reduced pressure
  2. dissolutionThe remainder was dissolved in EtOAc
  3. washthe resulting solution was washed with H2O until the pH of the aqueous phase
  4. washThe EtOAc solution was washed further with saturated aqueous Na2CO3
  5. dry with materialbefore being dried (MgSO4)
  6. filtrationFiltration and solvent evaporation

Sources & evidence

ORD record
ord-2675ce69ae3a470f8d12669a92399b79
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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