Acetophenone → 2-Methyl-6-phenyl-2,4-hexadien-6-one

HRID 1415463Notes

Reaction equation

HRID 1415463 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH:4]=O.[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])[CH3:8]>[O-2].[Zn+2]>[CH3:1][C:2](=[CH:3][CH:4]=[CH:8][C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 610203-Methyl-2-butenal

Product 1

HCID 540112072-Methyl-6-phenyl-2,4-hexadien-6-oneYield 87%

Reagents, catalysts & solvents 1

HCID 3007857Zinc OxideCatalyst

Procedure

50 Parts of 3,3-dimethylacrolein and 100 parts of acetophenone together with 10 parts of zinc oxide are kept for 3 hours at a temperature of 180° C under a pressure of 50 atmospheres. The reaction mixture is subjected to fractional distillation. 75.3 parts of 2-methyl-6-phenyl-2,4-hexadien-6-one (87% of theory based on 3,3-dimethylacrolein) is obtained at a conversion of 78% of theory. Boiling point: 107° to 110° C at 10116 4 mm.

Workup

  1. distillationThe reaction mixture is subjected to fractional distillation

Sources & evidence

ORD record
ord-0422a266067f415ca745860faebe689c
Source dataset
uspto-grants-1977_01
Patent number
US04005147

Reaction notes

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