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

HRID 2223445Notes

Reaction equation

HRID 2223445 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-7ed278263afa45129c6db2674cd8d386
Source dataset
uspto-grants-2008_05
Patent number
US07375204B2

Reaction notes

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