Thionyl Chloride → Benzene, (chloromethyl)phenoxy-

HRID 1034366Notes

Reaction equation

HRID 1034366 reaction equation
S(Cl)([Cl:3])=O.[O:5]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[O:5]([C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][Cl:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 36601112-Phenoxybenzyl alcohol

Product 1

HCID 169302Benzene, (chloromethyl)phenoxy-Yield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (1.92 ml) was added in one portion to a solution of 2-phenoxybenzyl alcohol (4.80 g) in dry dichloromethane (50 ml). The resulting mixture was stirred at room temperature for 2 hours, then washed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride, dried and concentrated under reduced pressure to give 2-phenoxybenzyl chloride (4.87 g, 93%) as a colourless oil.

Workup

  1. washwashed with water (×2), aqueous sodium bicarbonate (×2) and aqueous sodium chloride
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4297db7577bd4040a2e0d31c42cc17b3
Source dataset
uspto-grants-1994_05
Patent number
US05315025

Reaction notes

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