Acetone → HCID 2737469, compound

HRID 567140Notes

Reaction equation

HRID 567140 reaction equation
[F: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]>>[F: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 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 2737469HCID 2737469, compoundYield 82.3%

Procedure

In a 250 ml single neck flask was charged 12.4 g (100 mmoles,1.0 eq) of 4-fluorobenzaldehyde 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-(4-fluorophenyl)-3-buten-2-one as a faintly yellow oil in 82.3% 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-843ec1df30db4c12be592c5d9ec3e4b4
Source dataset
uspto-grants-2001_01
Patent number
US06177462B1

Reaction notes

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