2-Chloro-1-(4-cyclohexylphenyl)ethanone → 2,4-Dichlorobenzyl chloride

HRID 1389783Notes

Reaction equation

HRID 1389783 reaction equation
C1(C2C=CC(C(=O)C[Cl:13])=CC=2)CCCCC1.[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[CH2:20][Mg:21]Cl>CCOCC>[Mg:21].[Cl:17][C:18]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:19]=1[CH2:20][Cl:13]

Participants

5

Reactant 2

HCID 23637232-Chloro-1-(4-cyclohexylphenyl)ethanoneHCID 178478998HCID 178478998, compound

Product 2

HCID 72122,4-Dichlorobenzyl chlorideHCID 5462224Magnesium

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 47.3 g (0.2 mol) of 4-cyclohexylphenacyl chloride in 200 ml of ether is added dropwise to a solution of 0.4 mol of 2,4-dichlorobenzyl magnesium chloride, obtained from 10.6 g (0.44 mol) of magnesium and 78 g (0.4 mol) of 2,4-dichlorobenzyl chloride in 150 ml of ether. The reaction mixture is poured onto aqueous ammonium chloride solution and the ether phase is separated off, washed with water, dried over sodium sulphate and evaporated. 79.5 g (99% of theory) of 2-(4-cyclohexyl)-3-chloro-1-(2,4-dichlorophenyl)-propan-2-ol of refractive index nD20 =1.5780 are obtained.

Sources & evidence

ORD record
ord-f97221b48aa64113904549bfd860c1ef
Source dataset
uspto-grants-1981_01
Patent number
US04246274

Reaction notes

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