The Acid Product Obtained in the Synthesis of 2-Phenyltropone Derivatives from 2-Phenylsuberone

The acid hydrolysis of some polyhalotropones and some reactions of the products were investigated. The treatment of 2, 5-dichlorotropone with hydrochloric or sulfuric acid afforded 2chloro-5-hydroxytropone (I) and a small amount of 5-chlorotropolone. The compound I gives only-one kind of the methyl ether and one kind of the acetyl or benzoyl derivative. From the methyl ether, 5-amino-and 5-methylamino-2-chlorotropone were derived. The methoxyl and the amino groups of these compounds are reactive to alkaline hydrolysis, giving I without any of the skeletal rearrangement usually observed in the alkaline treatment of similar 2-halotropones. The hydrolysis of 2, 4, 7-tribromotropone with hydrochloric acid gave 3, 6-dichlorotropolone and 7-chloro-4-hydroxytropolone. unsaturated ketone.

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The Acid Product Obtained in the Synthesis of 2-Phenyltropone Derivatives from 2-Phenylsuberone

Cited by 3 publications

References 2 publications

Synthesis based on cyclohexadienes: Part 4. Novel synthesis of the 6-aryl-2,4-dimethoxybenzoates. Alternariol and methyl trimethylaltenusin

Synthesis based on cyclohexadienes: Part 4. Novel synthesis of the 6-aryl-2,4-dimethoxybenzoates. Alternariol and methyl trimethylaltenusin

The Mechanism of the Rearrangement Reaction of 3-Phenyl-4-methoxy-5-bromotropone to 3-Phenyl-4-methoxybenzoic Acid

The Synthesis and Reactions of 2-Chloro-5-hydroxytropone

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