Acetone → 4-(4-Chlorophenyl)-3-buten-2-one

HRID 567127Notes

Reaction equation

HRID 567127 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[OH-].[Na+].O.C(OCC)(=O)C.[CH3:19][C:20]([CH3:22])=[O:21]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[CH:19]/[C:20](=[O:21])[CH3:22])=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 77264-ChlorobenzaldehydeHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide

Product 1

HCID 7365724-(4-Chlorophenyl)-3-buten-2-oneYield 86.2%

Procedure

In a 250 ml single neck flask was charged 14 g (99.6 mmoles, 1.0 eq) of p-chlorobenzaldehyde dissolved in 30 ml of acetone. To this was added 5 g of 10% aqueous sodium hydroxide solution (12.5 mmoles, 0.125 eq), dropwise and during the course of addition, temperature was kept no higher than 25° C., while the mixture was agitated continuously for 30 minutes. To the mixture was added 50 ml of water, followed by 100 ml of ethyl acetate, the phases were separated and the organic phase was washed with water three times and then dried, and concentrated to obtain 15.5 g of (E)-4-(4-chlorophenyl)-3-buten-2-one as a faintly yellow oil in 86.2% yield.

Workup

  1. additiondropwise and during the course of addition, temperature
  2. customwas kept no higher than 25° C., while the mixture
  3. customthe phases were separated
  4. washthe organic phase was washed with water three times
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1279c2913d6843fd865cffb630edf2cc
Source dataset
uspto-grants-2001_01
Patent number
US06177462B1

Reaction notes

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