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

HRID 1885119Notes

Reaction equation

HRID 1885119 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](O)=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)[Cl:15]>C1C=CC=CC=1>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:15])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 16865Benzoic acid, 4-(acetyloxy)-HCID 24819Phosphorus pentachloride

Product 1

HCID 2756254p-Acetoxybenzoyl chlorideYield 104.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

10 g of p-acetyloxybenzoic acid was added to 45 ml of benzene, and 11.8 g of PCl5 was added little by little under stirring at room temperature. After 8.5 hours of heat-refluxing thereafter, the solvent was distilled off to obtain 11.5 g of p-acetyloxybenzoic acid chloride.

Workup

  1. additionwas added little by little
  2. temperatureAfter 8.5 hours of heat-refluxing
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-b70ede27eb5140309c2bbdf6c9ac60e9
Source dataset
uspto-grants-1992_09
Patent number
US05143643

Reaction notes

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