(5-Methyl-2-nitrophenyl)methanol → 5-Methyl-2-nitrobenzaldehyde

HRID 751483Notes

Reaction equation

HRID 751483 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH2:8][OH:9])[CH:7]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:7]=1)[CH:8]=[O:9]

Participants

4

Reactant 2

HCID 568847(5-Methyl-2-nitrophenyl)methanolHCID 2724130Cornforth reagent

Product 1

HCID 118051105-Methyl-2-nitrobenzaldehydeYield 79.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve (5-methyl-2-nitrophenyl)methanol (10 g, 59.88 mmol) in dichloromethane (210 mL). Add 3 Å molecular sieves (54 g) and pyridinium dichromate (22.53 g, 59.88 mmol). Stir at room temperature for 6 hours. Pass the crude reaction mixture through a short silica gel column, and remove under reduced pressure. Purification of the residue by flash chromatography (silica gel, 10-20% ethyl acetate:hexane) gives 7.84 g (79%) of title compound as colorless oil. 1H NMR (CDCl3) δ 10.41 (m, 1H), 8.02 (m, 1H), 7.69 (s, 1H), 7.53 (d, 1H), 2.51 (s, 3H).

Workup

  1. customPass the crude reaction mixture through a short silica gel column
  2. customremove under reduced pressure
  3. customPurification of the residue by flash chromatography (silica gel, 10-20% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-6dd11914fe4741ea80a24f6de04f8bfc
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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