Thionyl Chloride → 3,4,5-Triacetoxybenzoyl chloride

HRID 1632280Notes

Reaction equation

HRID 1632280 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:18][C:19](=[O:21])[CH3:20])[C:13]=1[O:14][C:15](=[O:17])[CH3:16])[C:8](O)=[O:9])(=[O:3])[CH3:2].S(Cl)([Cl:24])=O>ClCCCl>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:18][C:19](=[O:21])[CH3:20])[C:13]=1[O:14][C:15](=[O:17])[CH3:16])[C:8]([Cl:24])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 95088Benzoic acid, 3,4,5-tris(acetyloxy)-

Product 1

HCID 1555063,4,5-Triacetoxybenzoyl chlorideYield 102%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In 100 ml of 1,2-dichloroethane, 57 g (0.19 mol) of 3,4,5-triacetoxybenzoic acid and 34 g (0.29 mol) of thionyl chloride were reacted at 60° C. for 2 hours. The excess thionyl chloride and 1,2-dichloroethane were distilled away under reduced pressure to obtain 61 g of the desired product.

Workup

  1. distillationThe excess thionyl chloride and 1,2-dichloroethane were distilled away under reduced pressure

Sources & evidence

ORD record
ord-854325be44884b5b9d70cc1389794711
Source dataset
uspto-grants-1984_10
Patent number
US04474874

Reaction notes

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