Thionyl Chloride → (4-Chlorobutyl)benzene

HRID 484336Notes

Reaction equation

HRID 484336 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([CH2:11][CH2:12][CH2:13][CH2:14]O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)Cl>[C:5]1([CH2:11][CH2:12][CH2:13][CH2:14][Cl:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 76889Benzenebutanol

Product 1

HCID 78543(4-Chlorobutyl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 2.2 ml (20 mmol) amount of thionyl chloride was added dropwise to a methylene chloride solution (30 ml) containing 3 g (20 mmol) of 4-phenyl-1-butanol and stirred overnight at room temperature. The reaction solution was washed with water, an aqueous 50% sodium hydrogen carbonate solution, water, 1N hydrochloric acid and water in that order, and then the solvent was dried with anhydrous magnesium sulfate. After distillation under reduced pressure, 3.62 g of a crude 4-phenylbutyl chloride was obtained. This material was used in the next reaction without being further purified.

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialan aqueous 50% sodium hydrogen carbonate solution, water, 1N hydrochloric acid and water in that order, and then the solvent was dried with anhydrous magnesium sulfate
  3. distillationAfter distillation under reduced pressure

Sources & evidence

ORD record
ord-37bfb98eff5e43c98bfaca041e962d50
Source dataset
uspto-grants-1993_07
Patent number
US05231105

Reaction notes

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