Thionyl Chloride → 4-Methoxy-3-methylbenzoyl chloride

HRID 268378Notes

Reaction equation

HRID 268378 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5](O)=[O:6].S(Cl)([Cl:15])=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([Cl:15])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27595834-Methoxy-3-methylbenzoic Acid

Product 1

HCID 210929304-Methoxy-3-methylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 11.5 g. (0.07 mol.) of 3-methyl-4-methoxybenzoic acid and 10.7 g. (0.09 mol.) of thionyl chloride in 60 ml. of methylene chloride is refluxed on a steam bath for two hours. Concentration under reduced pressure and distillation of the residue gives 3-methyl-4-methoxybenzoic acid chloride, m.p. 37°-39°.

Workup

  1. concentrationConcentration
  2. distillationunder reduced pressure and distillation of the residue

Sources & evidence

ORD record
ord-825962360d5b436aa0ad301d11e764e5
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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