2-Methoxybenzoic acid → 2-Methoxybenzoyl chloride

HRID 1380154Notes

Reaction equation

HRID 1380154 reaction equation
[C:1]([OH:11])(=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.S(Cl)([Cl:14])=O>>[C:1]([Cl:14])(=[O:11])[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 113702-Methoxybenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 889692-Methoxybenzoyl chloride

Procedure

A mixture of 5 g of o-anisic acid and 10 ml of thionyl chloride was heated at 100° for about fifteen minutes. Excess thionyl chloride was removed under reduced pressure to give crude o-anisoyl chloride. The title compound was then prepared from 0.5 g of the title product of Example 3 using the general method of Example 14. Before recrystallization, however, the resultant solid was dissolved in water, made basic with 10% aqueous sodium carbonate, and extracted into dichloromethane. The extract was concentrated to dryness and the residue was purified by column chromatography on silica gel. Fractions containing the free base of the title compound were converted to the hydrochloride as in Example 2. Structure assignment was supported by the nmr spectrum and by elemental analysis.

Workup

  1. temperaturewas heated at 100° for about fifteen minutes
  2. customExcess thionyl chloride was removed under reduced pressure

Sources & evidence

ORD record
ord-0d3054c1518d4250855d53da75b54bc5
Source dataset
uspto-grants-1986_04
Patent number
US04579951

Reaction notes

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