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

HRID 341268Notes

Reaction equation

HRID 341268 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-70353601211840db8bfa8cf63b892398
Source dataset
uspto-grants-2014_11
Patent number
US08895752B2

Reaction notes

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