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

HRID 1611007Notes

Reaction equation

HRID 1611007 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-a07dcd0763c441409b1877b7235034c6
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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