4-Chloro-3-(methylsulfonyl)benzenemethanol → 4-Chloro-3-(methylsulfonyl)benzaldehyde

HRID 1532286Notes

Reaction equation

HRID 1532286 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[S:10]([CH3:13])(=[O:12])=[O:11]>ClCCl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[S:10]([CH3:13])(=[O:11])=[O:12]

Participants

4

Reactant 1

HCID 537575064-Chloro-3-(methylsulfonyl)benzenemethanol

Product 1

HCID 212517354-Chloro-3-(methylsulfonyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

4-Chloro-3-(methylsulfonyl)benzyl alcohol (1.0 g) was dissolved in dichloromethane (20 mL) and then active manganese(IV) oxide (4.2 g) was added and the mixture was stirred for 15 min at 22-28° C. The solid was removed by filtration and the filtrate was evaporated to dryness (yield 0.76 g). 1H-NMR (400 MHz, DMSO-d6) d=3.44 (s, 3H), 8.00 (d, J=8.2 Hz, 1H), 8.23 (dd, J=8.2 Hz, 2.2 Hz, 1H), 8.53 (d, J=2.2 Hz, 1H), 10.12 (s, 1H).

Workup

  1. customThe solid was removed by filtration
  2. customthe filtrate was evaporated to dryness (yield 0.76 g)

Sources & evidence

ORD record
ord-38643b0c443148999a01cff1a69cf01e
Source dataset
uspto-grants-2001_03
Patent number
US06201027B1

Reaction notes

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