Ethanol → 4-Methyl-4-(4-methylphenyl)-1-(3-phenoxyphenyl)pent-1-en-3-one

HRID 543265Notes

Reaction equation

HRID 543265 reaction equation
C(O)C.[CH3:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:16])([C:13](=[O:15])[CH3:14])[CH3:12])=[CH:7][CH:6]=1.[O:17]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[K+]>O>[O:17]([C:24]1[CH:25]=[C:26]([CH:27]=[CH:14][C:13](=[O:15])[C:11]([C:8]2[CH:9]=[CH:10][C:5]([CH3:4])=[CH:6][CH:7]=2)([CH3:16])[CH3:12])[CH:29]=[CH:30][CH:31]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 382843-PhenoxybenzaldehydeHCID 136032233-Methyl-3-(4-methylphenyl)butan-2-one

Product 1

HCID 545721994-Methyl-4-(4-methylphenyl)-1-(3-phenoxyphenyl)pent-1-en-3-oneYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 50 ml of ethanol were added 5.3 g of 2-(4-methylphenyl)-2-methyl-3-butanone, 6.0 g of 3-phenoxybenzaldehyde and 6.0 g of KOH, and the mixture was stirred at room temperature for one hour and 20 minutes. Then, the reaction mixture was poured into 300 ml of water and extracted with benzene. The benzene extract was washed with water and dried, and the solvent was evaporated under reduced pressure to give 10.4 g of crude 1-(3-phenoxyphenyl)-4-(4-methylphenyl)-4-methyl-1-penten-3-one. Then, the crude product was purified by column chromatography on 250 g of silica gel (eluent:benzene) to give 6.8 g of pure 1-(3-phenoxyphenyl)-4-(4-methylphenyl)-4-methyl-1-penten-3-one.

Workup

  1. extractionextracted with benzene
  2. extractionThe benzene extract
  3. washwas washed with water
  4. customdried
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ec50a8bf83244c6eb6e0c78c25776306
Source dataset
uspto-grants-1987_04
Patent number
US04661501

Reaction notes

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