4-Methoxybenzoic Acid → p-Anisoyl chloride

HRID 1080559Notes

Reaction equation

HRID 1080559 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.S(Cl)([Cl:14])=O>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:14])=[O:8])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 74784-Methoxybenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 7477p-Anisoyl chlorideYield 91%

Conditions

Temperature
80 °C

Procedure

7.6g of 4-methoxybenzoic acid was put in a 100 ml two-necked flask and dissolved by the addition of 50 ml of thionyl chloride, the solution was then refluxed at 80° C. for 2 hours. The reaction mixture was cooled to an ambient temperature and the precipitate was filtered out. Unreacted thionyl chloride was removed and the obtained product was vacuum distilled (185° C./2 mmHg). The yield was 91% and 1HNMR and IR spectra of the product were as follows.

Workup

  1. temperatureThe reaction mixture was cooled to an ambient temperature
  2. filtrationthe precipitate was filtered out
  3. customUnreacted thionyl chloride was removed
  4. distillationdistilled (185° C./2 mmHg)

Sources & evidence

ORD record
ord-8b91be740b104e278c95c7580d088340
Source dataset
uspto-grants-1996_12
Patent number
US05582766

Reaction notes

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