Thionyl Chloride → 1-Chloro-4-(chloromethyl)-2-methoxybenzene

HRID 2104252Notes

Reaction equation

HRID 2104252 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[CH:4][C:3]=1[O:10][CH3:11].S(Cl)([Cl:14])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][Cl:14])=[CH:4][C:3]=1[O:10][CH3:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 10910038(4-Chloro-3-methoxyphenyl)methanol

Product 1

HCID 576094431-Chloro-4-(chloromethyl)-2-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-chloro-3-methoxybenzyl alcohol (5 g, 1 equiv) in 15 mL of DCM was treated with thionyl chloride (5 mL, 3 equiv) at reflux for 2 hours. Evaporation of volatiles gave 4-chloro-3-methoxybenzyl chloride.

Workup

  1. temperatureat reflux for 2 hours
  2. customEvaporation of volatiles

Sources & evidence

ORD record
ord-52eddf484771457cb05304c56c958fe5
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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