Water → 4-Phenyl-2-hexanone
Reaction equation
[CH:1](=[CH:8]/[C:9](=[O:11])[CH3:10])\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.O.O1CCO[CH2:19][CH2:18]1>CCCCCC>[C:2]1([CH:1]([CH2:18][CH3:19])[CH2:8][C:9](=[O:11])[CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
143 mg of CuBr is added to 1.46 g (10 mmol) of cis/trans-benzylideneacetone (3-phenyl-but-3-en-2-one) in 20 ml of absolute dioxane. 11 ml (11 mmol) of a 1 molar solution of trimethyl aluminum in hexane is added to the reaction at room temperature under nitrogen atmosphere and, after completion of the addition, stirred for 10 minutes at 22° C. For hydrolysis of the reaction solution, 1 ml of water dissolved in 5 ml of dioxane is carefully added to the reaction. It is stirred for 10 minutes more and the inorganic precipitate filtered off with dioxane is washed again. The dioxane solution is concentrated by evaporation on a rotary evaporator and the residue is chromatographed on silica gel with ethyl acetate/hexane as eluent. After concentration by evaporation of the fractions, 1.37 g of 4-phenyl-hexan-2-one (78% of theory) is obtained a colorless liquid.
Workup
- additionafter completion of the addition
- additionis carefully added to the reaction
- stirringIt is stirred for 10 minutes more
- filtrationthe inorganic precipitate filtered off with dioxane
- washis washed again
- concentrationThe dioxane solution is concentrated by evaporation on a rotary evaporator
- customthe residue is chromatographed on silica gel with ethyl acetate/hexane as eluent
- concentrationAfter concentration
- customby evaporation of the fractions
Sources & evidence
- ORD record
- ord-4de833e154854154b7d17570addda2b8
- Source dataset
- uspto-grants-1999_06
- Patent number
- US05908944
Reaction notes
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