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

HRID 1395608Notes

Reaction equation

HRID 1395608 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-25a92c93e52d4a0dae669c9c329cea30
Source dataset
uspto-grants-1980_05
Patent number
US04204071

Reaction notes

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