Thionyl Chloride → 1-(Chloromethyl)-4-phenoxybenzene

HRID 1610310Notes

Reaction equation

HRID 1610310 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl>[Cl:18][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 826195(4-Phenoxyphenyl)methanol

Product 1

HCID 5209941-(Chloromethyl)-4-phenoxybenzeneYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (4-(phenyloxy)phenyl)methanol (8 g, 40.0 mmol) in chloroform (20 ml) was added thionyl chloride (36 ml, 500 mmol) and the mixture was heated under reflux overnight. The reaction solution was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate) to give 1-(chloromethyl)-4-(phenyloxy)benzene (8.1 g, 93%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction solution was concentrated
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-49799fdf43374421a052ef8955ad92b5
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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