Acetone → 3-Benzyl-4-fluorobenzaldehyde

HRID 1199835Notes

Reaction equation

HRID 1199835 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 g), 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-fluorobenzaldehdye (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
  4. customgave 3-benzyl-4-fluorobenzaldehdye (0.59 g), which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-76f7d7c8af6247b7b9c083691a26bbb1
Source dataset
uspto-grants-1990_02
Patent number
US04902814

Reaction notes

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