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

HRID 1982759Notes

Reaction equation

HRID 1982759 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-cd83324e56984ee69dc666e7fd463598
Source dataset
uspto-grants-2009_06
Patent number
US07541332B2

Reaction notes

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