Dimethylformamide → 3,4,5-Triacetoxybenzoyl chloride

HRID 5289

Reaction equation

HRID 5289 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].C(Cl)(=O)C([Cl:25])=O.CN(C)C=O>C(Cl)Cl>[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:25])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 95088Benzoic acid, 3,4,5-tris(acetyloxy)-

Product 1

HCID 1555063,4,5-Triacetoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,4,5-Triacetoxybenzoic acid (296.23 g, 1 mol) was slurried in a 2 L flask in CH2Cl2 (1.0 L), and oxalyl chloride (113 mL, 1.3 mol) as added, followed by slow, dropwise addition of N,N-dimethylformamide (1.5 mL). After 2 hours at RT, gas evolution had ceased, and 3,4,5-triacetoxybenzoyl chloride was isolated by evaporation under reduced pressure.

Sources & evidence

ORD record
ord-6fca121f54ad4dbeb09f154726606a7f
Source dataset
uspto-grants-1993_09
Patent number
US05244763

Linked notes

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