An Improved Synthesis of 2,7-Dihydroxytropone (3-Hydroxytropolone)

Hitoshi Takeshita; Akira Mori; Tomoyuki Kusaba

doi:10.1055/s-1986-31713

Synthesis 1986; 1986(7): 578-579
DOI: 10.1055/s-1986-31713

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An Improved Synthesis of 2,7-Dihydroxytropone (3-Hydroxytropolone)

Hitoshi Takeshita^* , Akira Mori, Tomoyuki Kusaba

^*Research Institute of Industrial Science, 86, Kyushu University, Kasuga-koen, Kasuga City, Fukuoka 816, Japan

Abstract

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2,7-Dihydroxytropone is efficiently prepared from 2-methoxytropone by bromination with N-bromosuccinimide, reaction of the resultant 2-bromo-7-methoxytropone with acetyl trifluoroacetate in situ, and hydrolysis of the 2,7-diacetoxytropone thus obtained with aqueous acetic acid. The intermediacy of a 2-acetoxy-1-bromo-3-methoxytropylium salt in the acetoxylation step is suggested.

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