2,3-Dimethyl-6-nitrobenzenemethanol → 2,3-Dimethyl-6-nitrobenzaldehyde

HRID 979526Notes

Reaction equation

HRID 979526 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH2:12][OH:13].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH:12]=[O:13]

Participants

5

Reactant 2

HCID 139370162,3-Dimethyl-6-nitrobenzenemethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 139370202,3-Dimethyl-6-nitrobenzaldehydeYield 93.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2,3-dimethyl-6-nitrobenzenemethanol (34.88 g, 0.192 mole) in dichloromethane (150 mL) was added to a stirred mixture of pyridinium chlorochromate (62.2 g, 0.288 mole) in dichloromethane (250 ml). The mixture was stirred vigorously for 4 hours, diluted with diethyl ether (500 mL) and the organic layer decanted. The residue was washed with diethyl ether (500 mL) and the combined organic solution filtered through a plug of silica gel (6"×11/2"). Evaporation of the solvent afforded 2,3-dimethyl-6-nitrobenzaldehyde (32.08 g, 93%). An analytical sample was prepared by crystallizing from diisopropyl ether and had m.p. 66°-68° C.

Workup

  1. customthe organic layer decanted
  2. washThe residue was washed with diethyl ether (500 mL)
  3. filtrationthe combined organic solution filtered through a plug of silica gel (6"×11/2")
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6899a719a9724c8dacf0fd3cc7f5d83a
Source dataset
uspto-grants-1987_05
Patent number
US04668686

Reaction notes

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