Water → (3-Methanesulfonylphenyl)methanol

HRID 641821Notes

Reaction equation

HRID 641821 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:9])(=[O:4])=[O:3].O>C(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH2:8][OH:9])[CH:10]=[CH:11][CH:12]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 962WaterHCID 135966023-(Methylsulfonyl)benzaldehyde

Product 1

HCID 23549738(3-Methanesulfonylphenyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH is added to a solution of 750 mg (4.08 mmol) 3-methanesulphonyl-benzaldehyde in 20 ml ethanol (see P. L. Ornstein, T. J. Bleisch, M. B. Arnold, R. A. Wright, B. G. Johnson, J. P. Tizzano, D. R. Helton, M. J. Kallman, D. D. Schoepp, M. Herin, J. Med. Chem. 1998, 41(3), 358-378 or B. Eistert, W. Schade, H. Selzer, Ber. 1964, 97(5), 1470-81). The reaction mixture is stirred at room temperature for 1 h. The reaction mixture is poured into water and extracted three times with ethyl acetate. The combined organic layers are washed with water and brine, dried, filtered and concentrated in vacuo to afford the title compound, used in the next step without further purification.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layers are washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b5c06863a0045e389c660cb9d5248d8
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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