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

HRID 234574Notes

Reaction equation

HRID 234574 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 chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
50 °C

Procedure

In a 200 ml-reaction vessel, 21.4 g (1.18×10-1M) of p-acetoxybenzoic acid and 80 ml of dry benzene were placed. To the mixture, 25.0 g (1.20×10-1M) of phosphorus pentachloride was added in 10 minutes at room temperature, followed by stirring for 3 hours at 50° C. After cooling, the solvent of the reaction mixture was distilled off to provide oily p-acetoxybenzoyl chloride.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent of the reaction mixture was distilled off

Sources & evidence

ORD record
ord-b9e49a89c8204c6093ab03d5d1decd65
Source dataset
uspto-grants-1997_01
Patent number
US05595685

Reaction notes

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