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

HRID 567134

Reaction equation

HRID 567134 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.[OH-].[Na+].O.C(OCC)(=O)C.[CH3:19][C:20]([CH3:22])=[O:21]>>[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[CH:19][C:20](=[O:21])[CH3:22])=[CH:3][CH:2]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 77254-MethylbenzaldehydeHCID 8857Ethyl AcetateHCID 14798Sodium Hydroxide

Product 1

HCID 1073884-(4-Methylphenyl)-3-buten-2-oneYield 84.3%

Procedure

In a 250 ml single neck flask was charged 12.1 g (100 mmoles,1.0 eq) of p-tolualdehyde 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 13.5 g of 4-(p-tolyl)-3-buten-2-one as a faintly yellow oil in 84.3% 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-2316b2d1c5d945f09eb0457f01df58c8
Source dataset
uspto-grants-2001_01
Patent number
US06177462B1

Linked notes

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