4-Methoxybenzoic Acid → p-Anisoyl chloride

HRID 904717Notes

Reaction equation

HRID 904717 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([OH:15])=O)=[CH:11][CH:12]=1>>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]([Cl:3])=[O:15])=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 74784-Methoxybenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 7477p-Anisoyl chloride

Procedure

25 g of thionyl chloride was added to 5 g of p-methoxybenzoic acid. After the temperature of the mixture was kept at 70° C. for 6 hours under reflux, the mixture was heated under reduced pressure to remove unchanged thionyl chloride. The residue was dissolved in benzene, and after the solution was heated to be condensed, it was cooled to produce precipitate. The precipitate was recrystallized with benzene to obtain p-methoxybenzoyl chloride. 10 mmol of choline chloride was added to 10 mmol of p-methoxybenzoyl chloride. The temperature of the mixture was kept at 120° C. for 5 hours. The residue was separated and purified by subjecting to silica gel chromatography to obtain p-methoxybenzoyl choline chloride.

Workup

  1. temperatureunder reflux
  2. temperaturethe mixture was heated under reduced pressure
  3. customto remove unchanged thionyl chloride
  4. dissolutionThe residue was dissolved in benzene
  5. temperatureafter the solution was heated
  6. customcondensed, it
  7. temperaturewas cooled
  8. customto produce precipitate
  9. customThe precipitate was recrystallized with benzene

Sources & evidence

ORD record
ord-ac642ce2a5384bc9950c91971307bec7
Source dataset
uspto-grants-1983_12
Patent number
US04419445

Reaction notes

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