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

HRID 354071Notes

Reaction equation

HRID 354071 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>CN(C=O)C.ClC1C=CC=CC=1>[Cl:16][C:9]([C:8]1[CH:12]=[CH:13][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=1)=[O:10]

Participants

5

Reactant 2

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

Product 1

HCID 2756254p-Acetoxybenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

A solution of 4-acetoxybenzoic acid (200 mg, 1.11 mmol), thionyl chloride(1.6 mL), 1 drop of DMF, and 7.5 mL of chlorobenzene was heated to 80° C. for 1.5 hrs. The reaction was then cooled to room temperature and the solvent and excess thionyl chloride were removed in vacuo. Theoretical yield of the title compound was assumed and the residue was used as is.

Workup

  1. customthe solvent and excess thionyl chloride were removed in vacuo

Sources & evidence

ORD record
ord-ec22449b153d4841a6c435cbe25bc9a9
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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