3-Methyl-4-nitrobenzyl alcohol → 3-Methyl-4-nitrobenzaldehyde

HRID 75797Notes

Reaction equation

HRID 75797 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH:11]=[O:12]

Participants

4

Reactant 2

HCID 5913603-Methyl-4-nitrobenzyl alcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 111945283-Methyl-4-nitrobenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-methyl-4-nitrophenyl)methanol (1.0 equiv.) in dichloromethane, pyridinium chlorochromate (1.1 equiv.) was added and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered through celite and the filtrate was evaporated. The residue was adsorbed on silica (100-200 mesh) and purified by flash chromatography on silica gel, eluting with 5% ethyl acetate in petroleum ether (60-80), to provide the title compound in the form of creamish crystals (93%); 1H NMR (300 MHz, CDCl3) δ: 2.66 (s, 3H), 7.84-7.87 (m, 2H), 8.04-8.07 (d, J=8.7 Hz, 1H), 10.12 (s, 1H); IR (KBr) 3104, 3079, 2981, 2857, 2743, 1702, 1607, 1518, 1383, 1361, 1308, 1226, 1153, 1008, 832, 735 cm−1.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate was evaporated
  3. custompurified by flash chromatography on silica gel
  4. washeluting with 5% ethyl acetate in petroleum ether (60-80)

Sources & evidence

ORD record
ord-261ccf64a29d41a0a833c005d184fa3e
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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