(3-Chloro-5-methoxyphenyl)methanol → 3-Chloro-5-methoxybenzaldehyde

HRID 387203Notes

Reaction equation

HRID 387203 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH2:5][OH:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6]

Participants

4

Reactant 2

HCID 12909342(3-Chloro-5-methoxyphenyl)methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 219046333-Chloro-5-methoxybenzaldehydeYield 77.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-chloro-5-methoxybenzyl alcohol (5.0 g, 28.9 mmol) and pyridinium chlorochromate (20% on alumina, 40 g, 37.8 mmol) was allowed to stir for 1.25 hr. Diethyl ether (200 ml) was then added followed by filtration of precipitate. The filtrate was concentrated under reduced pressure and the resulting residue was purified via silica gel chromatography using 40% dichloromethane, 60% petroleum ether as eluant, to give 3.8 g of 3-chloro-5-methoxybenzaldehyde. 1H-NMR (CDCl3): 3.84 (s, 3H) 7.13 (s, 1H), 7.28 (s, 1H), 7.41 (s, 1H), 9.89 (s, 1H).

Workup

  1. filtrationfollowed by filtration of precipitate
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified via silica gel chromatography

Sources & evidence

ORD record
ord-c9aabc7581f849409c3bf1ca26d9fefe
Source dataset
uspto-grants-2013_02
Patent number
US08372873B2

Reaction notes

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