4-Fluorophenethyl Alcohol → 2-(4-Fluorophenyl)acetaldehyde

HRID 2286797Notes

Reaction equation

HRID 2286797 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH:7]=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 820684-Fluorophenethyl AlcoholHCID 517045Sodium AcetateHCID 178418287HCID 178418287, compound

Product 1

HCID 111263222-(4-Fluorophenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To p-fluorophenethyl alcohol (4.5 g, 31.9 mmol) in 50 ml dichloromethane is added sodium acetate (0.5 g, 6.2 mmol) and pyridinium chlorochromate (10.4 g, 48.1 mmol) with stirring, at RT and under nitrogen. The reaction mixture is stirred for about 2 hours and then filtered through a column of Florisil using dichloromethane. The filtrate is dried, concentrated under vacuum and distilled (short path) to yield p-fluorophenylacetaldehyde (fraction at 90°, 3.5 mm Hq.).

Workup

  1. stirringThe reaction mixture is stirred for about 2 hours
  2. filtrationfiltered through a column of Florisil
  3. customThe filtrate is dried
  4. concentrationconcentrated under vacuum
  5. distillationdistilled (short path)

Sources & evidence

ORD record
ord-03435094b0b54da4a0dc22d19b555042
Source dataset
uspto-grants-1981_05
Patent number
US04267359

Reaction notes

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