[5-Chloro-2-(trifluoromethyl)phenyl]methanol → 5-Chloro-2-(trifluoromethyl)benzaldehyde

HRID 252088Notes

Reaction equation

HRID 252088 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([F:13])([F:12])[F:11])=[C:6]([CH2:8][OH:9])[CH:7]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([F:11])([F:12])[F:13])=[C:6]([CH:7]=1)[CH:8]=[O:9]

Participants

5

Reactant 2

HCID 2778112[5-Chloro-2-(trifluoromethyl)phenyl]methanolHCID 178418287HCID 178418287, compound

Product 1

HCID 177507585-Chloro-2-(trifluoromethyl)benzaldehydeYield 82.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve (5-chloro-2-trifluoromethylphenyl)-methanol (347 mg, 1.66 mmol) in dichloromethane (10 mL). Add pyridinium chlorochromate (717 mg, 3.32 mmol) and stir for 2 h. Dilute with diethyl ether and stir for 1 h. Filter and concentrate. Chromatograph on silica gel eluting with 10% ethyl acetate in hexane to give the title compound as a clear oil (285 mg, 82%). 1H NMR (400 MHz, MeOH-d4) 10.33 (s, 1H), 7.90 (s, 1H), 7.69 (d, 1H, J=8.4 Hz), 7.54 (d, 1H, J=8.4 Hz).

Workup

  1. filtrationFilter
  2. concentrationconcentrate

Sources & evidence

ORD record
ord-b1398ef446c54f61af22f6c1a0d40402
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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