Thionyl Chloride → 4-Chloro-2-methoxybenzoyl chloride

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5](=[CH:9][CH:10]=1)[C:6](O)=[O:7].S(Cl)([Cl:15])=O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:15])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 936824-Chloro-o-anisic acid

Product 1

HCID 221424504-Chloro-2-methoxybenzoyl chloride

Procedure

A solution of 2.0 g of 4-chloro-o-anisic acid in 22 ml of thionyl chloride is heated at reflux for 1 hour. The volatiles are evaporated in vacuo to give a residue which is concentrated from toluene three times and dried under vacuum to give 2.0 g of the desired product as a residue.

Workup

temperatureat reflux for 1 hour
customThe volatiles are evaporated in vacuo
customto give a residue which
concentrationis concentrated from toluene three times
customdried under vacuum

Sources & evidence

ORD record: ord-33ac9464e5e1486c8765991c4ac756d8
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05733905

Reaction notes

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