Phenacyl bromide → Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

HRID 842172Notes

Reaction equation

HRID 842172 reaction equation
[Na].[C:2]([O:8][CH2:9][CH3:10])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>C1(C)C=CC=CC=1>[CH2:9]([O:8][C:2](=[O:7])[CH:3]([CH2:12][C:13](=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:4](=[O:5])[CH3:6])[CH3:10]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8868Ethyl AcetoacetateHCID 5360545Sodium2×

Product 1

HCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Sodium metal (60 mmol, 1.4 g) was suspended in 80 mL (milliliter) toluene under nitrogen. Ethyl acetoacetate (88 mmol (millimole), 11.4 g) was added dropwise, and the resulting mixture was stirred until all sodium was consumed. The reaction mixture then was cooled in an ice bath (0-5° C.) and 2-bromoacetophenone (60 mmol, 12 g) in 140 mL toluene was added dropwise. The reaction was stirred overnight with gradual warming to room temperature. Analysis of the reaction mixture by GC and TLC showed that the reaction was complete. The reaction mixture then was washed with 200 mL water, then the organic and aqueous layers were separated. The organic layer was dried over MgSO4 (magnesium sulfate). The toluene was removed from the organic layer under vacuum to provide a yellow oil which was purified by Kugelrohr distillation (b.p. 135-145° C. at 0.35 Torr.).

Workup

  1. customwas consumed
  2. additionwas added dropwise
  3. washThe reaction mixture then was washed with 200 mL water
  4. customthe organic and aqueous layers were separated
  5. dry with materialThe organic layer was dried over MgSO4 (magnesium sulfate)
  6. customThe toluene was removed from the organic layer under vacuum
  7. customto provide a yellow oil which
  8. distillationwas purified by Kugelrohr distillation (b.p. 135-145° C. at 0.35 Torr.)

Sources & evidence

ORD record
ord-ac05854deede4537939fb9ec984146ff
Source dataset
uspto-grants-2002_04
Patent number
US06372777B1

Reaction notes

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