Acetone → 3-Benzyl-4-fluorobenzaldehyde

HRID 1200069Notes

Reaction equation

HRID 1200069 reaction equation
[CH2:1]([C:8]1[CH:9]=[C:10]([CH:15]2OCC[O:16]2)[CH:11]=[CH:12][C:13]=1[F:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.O>S(=O)(=O)(O)O.C(OCC)C>[CH2:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[F:14])[CH:15]=[O:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 138542792-(3-Benzyl-4-fluorophenyl)-1,3-dioxolane

Product 1

HCID 138542803-Benzyl-4-fluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(3-benzyl-4-fluorophenyl)-1,3-dioxolane (0.7 h) acetone (10 cm3), water (1 cm3) and concentrated sulphuric acid (5 drops) was stirred for 16 hours. The reaction mixture was poured into diethyl ether and the organic layer washed with sodium bicarbonate solution, water and brine, then dried over anhydrous magnesium sulphate. Evaporation of the solvents under reduced pressure gave 3-benzyl-4-fluorobenzaldehyde (0.59 g), which was used without further purification.

Workup

  1. washthe organic layer washed with sodium bicarbonate solution, water and brine
  2. dry with materialdried over anhydrous magnesium sulphate
  3. customEvaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-b49798a3a0024638bda4bf0677344cd2
Source dataset
uspto-grants-1990_02
Patent number
US04904677

Reaction notes

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