1-(Triphenylphosphoranylidene)acetone → 6-(p-Benzyloxyphenyl)-3,5-hexadien-2-one

HRID 443959Notes

Reaction equation

HRID 443959 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([CH:13]=[CH:14][CH:15]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([CH:22]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:21])[CH3:20]>C1(C)C(C)=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([CH:13]=[CH:14][CH:15]=[CH:20][C:19](=[O:21])[CH3:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 54136827p-Benzyloxycinnamaldehyde

Product 1

HCID 544626506-(p-Benzyloxyphenyl)-3,5-hexadien-2-oneYield 79.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 19.7 g of p-benzyloxycinnamaldehyde and 27.6 g of acetylmethylenetriphenylphosphorane in 190 ml of xylene was heated under reflux for 2 hours, the solvent was then evaporated and the residual crystals were recrystallized from benzene to give 18.3 g of the desired compound melting at 132°-133° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customthe solvent was then evaporated
  3. customthe residual crystals were recrystallized from benzene

Sources & evidence

ORD record
ord-2b5a0f9f15a543619f8fff2902e8b7d8
Source dataset
uspto-grants-1981_04
Patent number
US04262013

Reaction notes

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