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

HRID 705462Notes

Reaction equation

HRID 705462 reaction equation
[OH-].[Na+].[CH:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][C:12]([CH3:14])=[O:13]>CCO>[C:4]1(/[CH:3]=[CH:11]/[C:12](=[O:13])/[CH:14]=[CH:3]/[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 240BenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 640180(1E,4E)-1,5-Diphenyl-1,4-pentadien-3-oneYield 788.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of aq. NaOH solution (2 N, 125 mL) in EtOH (250 mL) was added to a mixture of benzaldehyde (26.5 g, 25 mmol) in acetone (9.2 mL, 13 mmol). The reaction mixture was stirred for 4 h at ambient temperature and the resulting yellow precipitate was filtered, washed with H2O, recrystallized from EtOAc and dried in vacuo to obtain NW275 as a yellow solid (23.1 g, 79%). mp: 106-107° C. 1H NMR (250 MHz, CDCl3) δ (ppm): 7.78 (d, 3J=16.0 Hz, 2H, Hvin), 7.66-7.64 (m, 4H, HAr), 7.46-7.44 (m, 6H, HAr), 7.12 (d, 3J=16.0 Hz, 2H, Hvin). 13C NMR (75 MHz, CDCl3) δ (ppm): 189.3 (C), 143.7 (CH), 135.2 (C), 130.9 (CH), 129.4 (CH), 128.8 (CH), 125.8 (CH). MS (EI) m/z: 234.2 (M+). Anal. calcd for C17H14O: C, 87.15; H, 6.02. Found: C, 87.03; H, 6.03%.

Workup

  1. filtrationthe resulting yellow precipitate was filtered
  2. washwashed with H2O
  3. customrecrystallized from EtOAc
  4. customdried in vacuo

Sources & evidence

ORD record
ord-fce66fd3d39a4bc7b207962891af3bb0
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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