Thionyl Chloride → Benzene, 1-butyl-4-(chloromethyl)-

HRID 1673075Notes

Reaction equation

HRID 1673075 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13]O)=[CH:11][CH:10]=1)[CH2:6][CH2:7][CH3:8]>CCOCC>[Cl:3][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5782884-Butylbenzyl alcohol

Product 1

HCID 182273Benzene, 1-butyl-4-(chloromethyl)-Yield 104.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionyl chloride (2.5 ml, 34 mmol) was added to a solution of 4-n-butylbenzyl alcohol (2.0 g, 12 mmol) in ether (25 ml), and this mixture was stirred at room temperature for 3 hours. After concentration of the mixture, excess thionyl chloride was removed by azeotropic distillation with benzene to give the title compound (2.3 g). This compound was used in the following reaction without purification.

Workup

  1. customAfter concentration of the mixture, excess thionyl chloride was removed by azeotropic distillation with benzene

Sources & evidence

ORD record
ord-cdcb9722f80d444f89a72ff093481e10
Source dataset
uspto-grants-2011_08
Patent number
US07999090B2

Reaction notes

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