Benzoate → 3-Methylflavone-8-carboxylic acid

HRID 1981914Notes

Reaction equation

HRID 1981914 reaction equation
[C:1]([O:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])(=O)[CH2:2][CH3:3].[Cl-].[Al+3].[Cl-].[Cl-].C(CC(O)C([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O)(O)=O.[C:33](OC(=O)C1C=CC=CC=1)(=[O:40])C1C=CC=CC=1.C([O-])(=O)C1C=CC=CC=1>>[CH3:3][C:2]1[C:33](=[O:40])[C:14]2[C:6](=[C:7]([C:8]([OH:10])=[O:9])[CH:11]=[CH:12][CH:13]=2)[O:5][C:1]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 5

HCID 242BenzoateHCID 7167Benzoic anhydrideHCID 959382-Propionyloxybenzoic acidHCID 6451240Aluminum(III) ChlorideHCID 54465964HCID 54465964, compound

Product 1

HCID 770163-Methylflavone-8-carboxylic acid

Procedure

Thus, 2-propionyloxybenzoic acid is heated with anhydrous aluminum chloride in a Fries rearrangement and the resulting 3-carboxy-2-hydroxypropiophenone is heated with benzoic anhydride and alkali benzoate at 180° to 190° C. to afford 3-methylflavone-8-carboxylic acid derivatives.

Sources & evidence

ORD record
ord-a777d37c13a04c7ca46c3340f8de3cad
Source dataset
uspto-grants-1986_06
Patent number
US04594345

Reaction notes

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