Benzoic acid, 4-(acetyloxy)- → p-Acetoxybenzoyl chloride

HRID 1644761Notes

Reaction equation

HRID 1644761 reaction equation
S(Cl)([Cl:3])=O.[C:5]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](O)=[O:14])=[CH:11][CH:10]=1)(=[O:7])[CH3:6]>C1(C)C=CC=CC=1>[C:5]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([Cl:3])=[O:14])=[CH:11][CH:10]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 16865Benzoic acid, 4-(acetyloxy)-HCID 24386Thionyl Chloride

Product 1

HCID 2756254p-Acetoxybenzoyl chlorideYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (11.1 mL, 15.3 mmol) was added to 4-acetoxybenzoic acid (2.50 g, 13.9 mmol), and the reaction was warmed to reflux. The reaction was cooled after heating for 3.5 hours, and concentrated in vacuo to give a colorless oil. Toluene was added to the residue and the mixture was concentrated in vacuo to remove any residual thionyl chloride. This process was repeated twice more to give 510 (2.54 g, 92%) as a colorless oil. This material was used in the next step without additional purification.

Workup

  1. temperaturethe reaction was warmed to reflux
  2. temperatureThe reaction was cooled
  3. temperatureafter heating for 3.5 hours
  4. concentrationconcentrated in vacuo
  5. customto give a colorless oil
  6. concentrationthe mixture was concentrated in vacuo
  7. customto remove any residual thionyl chloride

Sources & evidence

ORD record
ord-c63b2dfa231f4deb8593ff8da19e2209
Source dataset
uspto-grants-2012_02
Patent number
US08124632B2

Reaction notes

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