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A synthesis of α-anhydrotrimethylbrazilone

✍ Scribed by K.W. Bentley; R. Robinson

Publisher
Elsevier Science
Year
1959
Tongue
French
Weight
174 KB
Volume
1
Category
Article
ISSN
0040-4039

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✦ Synopsis

WE wish to record a synthesis of a-anhydrotrimethylbrazilone (I) that was carried to the penultimate stage in 1947. Condensation of 1,3-dimethoxybenzene and veratroyl chloride in boiling benzene with aluminium chloride afforded an excellent yield of 2-hydroxy-4,3',4'-trimethoxybenzophenone (II), instead of the tetramethoxy-compound reported 1 to result from this reaction below 4'0'. This preparation of the phenol (II) appears to be superior to those previously described.2" Condensation of the phenol (II) with bromoacetone and treatment of the product with alkali gave P-acetyl-j-(3',4'-dimethoxyphenyl)-6-methoxycoumarone (III), which may be regarded as a dihydro-a-anhydrotrimeth.ylbrazilone.

Bromination of this ketone with N-bromosuccinimide proceeded slowly, giving a non-crystalline bromo-compound that affqrded a-anhydrotrimethylbrazilone (I) in poor yield on treatment with aluminium chloride in benzene. The low yield of (I) may be attributed at least in part to the production of nuclear as '

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