3-(4-Methoxyphenyl)-1-propanol → 3-(4-Methoxyphenyl)propanal

HRID 567884Notes

Reaction equation

HRID 567884 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:5][CH:4]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 794063-(4-Methoxyphenyl)-1-propanolHCID 178418287HCID 178418287, compound

Product 1

HCID 111266073-(4-Methoxyphenyl)propanalYield 45.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-(4-methoxyphenyl)propan-1-ol (15.02 g) in dichloromethane (100 ml) was added to a stirred suspension of pyridinium chlorochromate (29 g) in dichloromethane (250 ml). The mixture was stirred for 2 hours then filtered through a kieselguhr pad. The residue was washed with ether (3×500 ml) and the combined liquors were evaporated under reduced pressure. The residual oil was purified by vacuum distillation to give the subtitle compound (6.81 g) as an oil.

Workup

  1. filtrationthen filtered through a kieselguhr pad
  2. washThe residue was washed with ether (3×500 ml)
  3. customthe combined liquors were evaporated under reduced pressure
  4. distillationThe residual oil was purified by vacuum distillation

Sources & evidence

ORD record
ord-8da3e7c5eaec4779a62c457ffce09dd1
Source dataset
uspto-grants-2001_01
Patent number
US06180635B2

Reaction notes

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