Thionyl Chloride → 3-Phenoxybenzyl chloride

HRID 1610317Notes

Reaction equation

HRID 1610317 reaction equation
[C:1]1([O:7][C:8]2[CH:9]=[C:10]([CH2:14]O)[CH:11]=[CH:12][CH:13]=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:10]1[CH:11]=[CH:12][CH:13]=[C:8]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 262953-Phenoxybenzyl alcohol

Product 1

HCID 932913-Phenoxybenzyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (3-(phenyloxy)phenyl)methanol (10 g, 49.4 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)-3-(phenyloxy)benzene (10.7 g, 98%).

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-b3efb8f78fb24b4292a8e9230ceadaa0
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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