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

HRID 2372239Notes

Reaction equation

HRID 2372239 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].S(Cl)([Cl:16])=O>>[C:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([Cl:16])=[O:10])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 16865Benzoic acid, 4-(acetyloxy)-HCID 24386Thionyl Chloride2×

Product 1

HCID 2756254p-Acetoxybenzoyl chloride

Procedure

After heating and refluxing 1.4 g (8.0 mmol) of 4-acetoxybenzoic acid and 6 ml of thionyl chloride, surplus thionyl chloride was removed, and 4-acetoxybenzoic acid chloride was obtained. Then, a mixed solution of 1.7 g of the hydrazide obtained in Step 1, 1 ml of pyridine and 15 ml of dioxane was added to the 4-acetoxybenzoic acid chloride and the mixture was heated and refluxed for two hours. After the reaction was completed, 2.6 g (7.0 mmol) of dihydrazide was obtained by pouring a 50 ml solution of salt, filtering and cleaning the crystals which had deposited, by water and methanol.

Workup

  1. temperatureAfter heating
  2. customwas removed

Sources & evidence

ORD record
ord-545f54f3fe504ceb8e7e0f438af0f197
Source dataset
uspto-grants-1992_03
Patent number
US05098600

Reaction notes

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