Benzene → Acetic Anhydride

HRID 328592

Reaction equation

HRID 328592 reaction equation
[C:1]([C:4]1[C:5](=[O:15])[O:6][C:7]([OH:14])=[C:8]([C:11](=[O:13])[CH3:12])[C:9]=1[OH:10])(=[O:3])[CH3:2].C1C=CC=CC=1.C1(C)C=CC=CC=1.C[OH:30]>S(=O)(=O)(O)O>[C:1]([C:4]1[C:5](=[O:15])[O:6][C:7]([OH:14])=[C:8]([C:11](=[O:13])[CH3:12])[C:9]=1[OH:10])(=[O:3])[CH3:2].[CH2:8]([C:7]([OH:6])=[O:14])[C:9]([CH2:4][C:5]([OH:15])=[O:30])=[O:10].[C:5]([O:6][C:7](=[O:14])[CH3:8])(=[O:15])[CH3:4]

Participants

8

Reactant 4

HCID 241BenzeneHCID 887MethanolHCID 1140TolueneHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Product 3

HCID 7918Acetic AnhydrideHCID 68328Acetonedicarboxylic acidHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The starting materials of formula II above used herein are generally prepared by reaction of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one with the appropriate amine (RNH2). The reactants are usually heated at reflux in an inert organic solvent such as benzene, toluene or methanol for from two to twelve hours. 3,5-Diacetyl-4,6-dihydroxy-2H-pyran-2-one is obtained by reaction of acetonedicarboxylic acid and acetic anhydride in sulfuric acid at elevated temperature.

Workup

  1. temperatureThe reactants are usually heated

Sources & evidence

ORD record
ord-a4080139efa24d0e88eb74d17b34b454
Source dataset
uspto-grants-1977_04
Patent number
US04017633

Linked notes

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