MAGNESIUM SILICATE (synthetic) → (3-Fluorophenyl)acetaldehyde

HRID 1590603Notes

Reaction equation

HRID 1590603 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[F:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][OH:21])[CH:16]=[CH:17][CH:18]=1.[O-][Si]([O-])=O.[Mg+2]>ClCCl>[F:12][C:13]1[CH:14]=[C:15]([CH2:19][CH:20]=[O:21])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 61680MAGNESIUM SILICATE (synthetic)HCID 5731322-(3-Fluorophenyl)ethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 15811999(3-Fluorophenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of pyridinium chlorochromate (75.5 g, 0.35 mol) in dry dichloromethane (300 ml) under a nitrogen atmosphere was added 2-(3-fluorophenyl)ethanol (43 g, 0.31 mol) dropwise. After the addition the mixture was stirred for 1 hour, allowed to stand overnight then poured down a florisil column. The column was washed with ether and the combined filtrate and washings were evaporated to leave the crude 3-fluorophenyl acetaldehyde as an unstable liquid which was not purified further (34 g), NMR δ 9.75 (1H, t), 7.3 (1H, m), 7.05-6.9 (3H, m), 3.7 (2H, d).

Workup

  1. additionAfter the addition the mixture
  2. waitto stand overnight
  3. washThe column was washed with ether
  4. customthe combined filtrate and washings were evaporated

Sources & evidence

ORD record
ord-c9a4d3174601417393b412ee412f3e08
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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