(3-Methanesulfonylphenyl)methanol → 3-(Methylsulfonyl)benzaldehyde

HRID 858623Notes

Reaction equation

HRID 858623 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH2:11][OH:12])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH:11]=[O:12])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 23549738(3-Methanesulfonylphenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 135966023-(Methylsulfonyl)benzaldehydeYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [3-(methylsulfonyl)phenyl]methanol (680 mg, 3.66 mmol) in anhydrous CH2Cl2 (20 mL) was treated with PCC (1.03 g, 4.75 mmol) at room temperature for 2 hours. The solvent was removed and the residue was purified by flash column chromatography (20–60% EtOAc in hexanes) to give the product (500 mg, 74% yield). 1H NMR (300 MHz, CDCl3) δ: 3.13 (s, 3 H), 7.77–7.82 (m, 1 H), 8.18–8.24 (m, 2 H), 8.46–8.48 (m, 1 H), 10.12 (s, 1 H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash column chromatography (20–60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7137ac6553384accbcc5d25f127b0aaa
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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