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

HRID 2093003Notes

Reaction equation

HRID 2093003 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-0f951a0640a14e9994e37310716f99ea
Source dataset
uspto-grants-2013_05
Patent number
US08440706B2

Reaction notes

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