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

HRID 2038548Notes

Reaction equation

HRID 2038548 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 78%

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 (78%). 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-028a84b18aab4ce3a771fe6c2ed8443e
Source dataset
uspto-grants-2013_11
Patent number
US08575208B2

Reaction notes

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