2-(2-Fluorophenyl)ethan-1-ol → (2-Fluorophenyl)acetaldehyde

HRID 1924872Notes

Reaction equation

HRID 1924872 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH:5]=[O:6]

Participants

4

Reactant 2

HCID 27332962-(2-Fluorophenyl)ethan-1-ol2×HCID 178418287HCID 178418287, compound2×

Product 1

HCID 17770161(2-Fluorophenyl)acetaldehydeYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-fluorophenethyl alcohol (Intermediate C1) (commercially available from Aldrich) (2.8 g, 20 mmol) in CH2Cl2 at −10° C. was oxidized by action of pyridinium chlorochromate: PCC (5 g, 23 mmol) in the presence of Celite (10 g) for 1 h at −10° C. and a couple hours at rt. The mixture was filtered through silica gel and the solvent was removed under vacuum to give (2-fluoro-phenyl)-acetaldehyde (Intermediate C2) 2.8 g (99%).

Workup

  1. customat rt
  2. filtrationThe mixture was filtered through silica gel
  3. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ebce1716719c46e6b97b0d56059ad595
Source dataset
uspto-grants-2012_05
Patent number
US08178571B2

Reaction notes

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