Thionyl Chloride → 3,5-Dichlorobenzyl chloride

HRID 966413Notes

Reaction equation

HRID 966413 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[CH2:9]O>C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([Cl:14])[CH:13]=1)[CH2:9][Cl:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 432363,5-Dichlorobenzylic alcohol

Product 1

HCID 1378803,5-Dichlorobenzyl chlorideYield 99.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
45 °C

Procedure

A solution of 12.5 g of thionyl chloride in 20 ml of chloroform is added dropwise, at RT, to a solution of 14.5 g of 3,5-dichlorobenzyl alcohol in 150 ml of chloroform, followed by heating at 40-50° C. for 8 hours and stirring at RT overnight. The mixture is concentrated under vacuum to give 16 g of the expected product, which is used without further processing.

Workup

  1. concentrationThe mixture is concentrated under vacuum

Sources & evidence

ORD record
ord-7060929e7eec4704a3d68e56b970c050
Source dataset
uspto-grants-2005_10
Patent number
US06951940B2

Reaction notes

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