Acetone → Dibenzylidene acetone

HRID 130571Notes

Reaction equation

HRID 130571 reaction equation
[OH-].[Na+].[CH2:3]([OH:5])[CH3:4].[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:14][C:15]([CH3:17])=O>>[CH:6](=[CH:4][C:3]([CH:14]=[CH:15][C:17]1[CH:11]=[CH:12][CH:7]=[CH:8][CH:9]=1)=[O:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 4

HCID 180Acetone2×HCID 240Benzaldehyde2×HCID 702EthanolHCID 14798Sodium Hydroxide

Product 1

HCID 95417Dibenzylidene acetone

Procedure

To an aqueous solution of sodium hydroxide (200 grams (g) in one liter of water) was added ethanol (1.6 liters; purity greater than 95%) and the resultant mixture was stirred well. Another mixture having acetone (29 g) and benzaldehyde (106 g) was added to this solution under stirring. A yellow colored precipitate was observed. The stirring was continued for about 15 minutes (min). Subsequently additional acetone (29 g) and benzaldehyde (106 g) were added and the mixture was stirred for another 45 min. The yellow colored precipitate was separated by filtration, washed with water (2 liters), and dried at room temperature to get 223 g of crude dibenzalacetone. Melting point of the compound was obtained as 104-106° C. This product was used in the next step without further purification.

Workup

  1. additionwas added to this solution
  2. stirringthe mixture was stirred for another 45 min
  3. customThe yellow colored precipitate was separated by filtration
  4. washwashed with water (2 liters)
  5. customdried at room temperature

Sources & evidence

ORD record
ord-98bf2159bdca4496b99a0f51b7b05868
Source dataset
uspto-grants-2008_06
Patent number
US07381786B2

Reaction notes

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