Acetone → (1E,4E)-1,5-Diphenyl-1,4-pentadien-3-one

HRID 2113929Notes

Reaction equation

HRID 2113929 reaction equation
[OH-].[Na+].[CH3:3][C:4]([CH3:6])=[O:5].[CH:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.C(O)C>[C:8]1(/[CH:7]=[CH:3]/[C:4](=[O:5])/[CH:6]=[CH:7]/[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 240BenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 640180(1E,4E)-1,5-Diphenyl-1,4-pentadien-3-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

(3) Hill and Barbaro, Experiments in Organic Chemistry. Contemporary Publishing Co. of Raleigh, Inc., Raleigh, 1996. 5 g of sodium hydroxide, dissolved in 25 ml of water and 25 ml of 95% ethanol, was cooled to 20 to 25° C. 2.9 g (50 mmol) of acetone and 10.6 g (100 mmol) of benzaldehyde were added, and a yellow precipitate formed. After 20 minutes the solution was filtered, and the solid was recrystallized from ethyl acetate to afford 10.1 g (86.3%) of bright-yellow platelets: mp 111.9-112.5° C. (lit. mp 112° C., Hill and Barbaro, supra). 1H NMR (250 MHz) δ 7.79-7.73 (d, 1 H), 7.65-7.61 (m, 4 H), 7.44-7.41 (t, 6 H), 7.13-7.07 (d, 1 H) ppm.

Workup

  1. customa yellow precipitate formed
  2. filtrationAfter 20 minutes the solution was filtered
  3. customthe solid was recrystallized from ethyl acetate
  4. customto afford 10.1 g (86.3%) of bright-yellow platelets

Sources & evidence

ORD record
ord-21cd4852e66c40c8a5425fb13a9db9e8
Source dataset
uspto-grants-2008_10
Patent number
US07432303B2

Reaction notes

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