alpha-Hydroxyacetophenone → Benzoylacetone

HRID 1282248Notes

Reaction equation

HRID 1282248 reaction equation
OCC(C1C=CC=CC=1)=O.[Na].[C:12]([CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17])(=[O:14])[CH3:13].[Na]>C(OCC)(=O)C>[C:12]([CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 68490alpha-HydroxyacetophenoneHCID 5360545SodiumHCID 70140380HCID 70140380, compound

Product 1

HCID 7166BenzoylacetoneYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-hydroxyacetophenone (20 g) is dissolved in ethyl acetate (200 ml). Sodium powder (16 g) is gradually added in 15-20 minutes, so to maintain a reasonable reflux. The mixture is refluxed for 1 hour, then it is allowed to cool. Grinded ice (200 g) is then added until precipitation of sodium acetylacetophenone, which is then isolated by filtration under vacuum. The solid product is then crystallised with acetic acid 40% (200 ml), obtaining acetyl acetophenone (19.6 g) as pulverulent crystals (m.p.=95° C.; yield=75%).

Workup

  1. temperatureso to maintain a reasonable reflux
  2. temperatureThe mixture is refluxed for 1 hour
  3. temperatureto cool
  4. customis then isolated by filtration under vacuum
  5. customThe solid product is then crystallised with acetic acid 40% (200 ml)

Sources & evidence

ORD record
ord-d409c9a41f3f41d18d0cae0172a85ddd
Source dataset
uspto-grants-2002_09
Patent number
US06455578B1

Reaction notes

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