Dichloromethane → 5-Methyl-2-nitrobenzaldehyde

HRID 274129Notes

Reaction equation

HRID 274129 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(Cl)Cl.[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([N+:24]([O-:26])=[O:25])=[C:20]([CH:23]=1)[CH2:21][OH:22]>C(OCC)C>[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([N+:24]([O-:26])=[O:25])=[C:20]([CH:23]=1)[CH:21]=[O:22]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 568847(5-Methyl-2-nitrophenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 118051105-Methyl-2-nitrobenzaldehydeYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyridinium chlorochromate (25.0 g, 116 mmol) was added to methylene chloride (65 ml) while stirring, and then thereto was added 5-methyl-2-nitrobenzyl alcohol (12.9 g, 77.3 mmol). The mixture was stirred at room temperature for 15 hours, and diethyl ether (155 ml) was added. The ether layer was removed by decantation. Diethyl ether (30 ml) was added to the residue, and the ether layer was removed by decantation (3 times). The ether layers were combined, and passed through 15.5 g of silica gel. The obtained solution was concentrated, and subjected to flash chromatography on silica gel using a mixed solvent of hexane/ethyl acetate (8:1), whereby 10.6 g of 5-methyl-2-nitrobenzaldehyde was obtained.

Workup

  1. stirringThe mixture was stirred at room temperature for 15 hours
  2. customThe ether layer was removed by decantation
  3. additionDiethyl ether (30 ml) was added to the residue
  4. customthe ether layer was removed by decantation (3 times)
  5. concentrationThe obtained solution was concentrated

Sources & evidence

ORD record
ord-88f3783cd3fb411aa317f8278adf9af4
Source dataset
uspto-grants-1995_02
Patent number
US05387684

Reaction notes

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