Ethanone, 1-(1,1'-biphenyl)-4-yl-2-chloro- → Benzyl Chloride

HRID 1702455Notes

Reaction equation

HRID 1702455 reaction equation
[C:1]1([C:7]2C=CC(C(=O)CCl)=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Mg:24][Cl:25])C1C=CC=CC=1>C(OCC)C>[Mg:24].[CH2:7]([Cl:25])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 69463Ethanone, 1-(1,1'-biphenyl)-4-yl-2-chloro-HCID 178418336HCID 178418336, compound

Product 2

HCID 7503Benzyl ChlorideHCID 5462224Magnesium

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

115.3 g (0.5 mol) of 4-phenylphenacyl chloride are added portions to a solution of benzyl-magnesium chloride, obtained from 24.3 g (1 mol) of magnesium and 115 ml (1 mol) of benzyl chloride in 150 ml of diethyl ether. The reaction mixture is warmed under reflux for 90 minutes and then poured onto aqueous ammonium chloride solution. The ether phase is separated off, washed with water, dried over sodium sulphate and concentrated. The oil which remains is made to crystallise by stirring with petroleum ether. 50 g (31% of theory) of 2-(4-biphenylyl)-3-chloro-1-phenylpropan-2-ol of melting point 96° C. are obtained.

Sources & evidence

ORD record
ord-ef97697eeb914fa89d4c10e0af364c10
Source dataset
uspto-grants-1983_04
Patent number
US04381306

Reaction notes

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