Journal of Organic Chemistry

Synthesis and chemistry of octamethylnaphthalene

H Hart, A Oku

Index: Hart,H.; Oku,A. Journal of Organic Chemistry, 1972 , vol. 37, p. 4269 - 4274

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Citation Number: 26

Abstract

A five-step synthesis of octamethylnaphthalene (1) from hexamethylbenzene, overall yield 5l%, is described. Addition of 3, 6-dimethylbenzyne to hexamethyl-2, 4-cyclohexadienone (2) gave adduct 3 which with dimsyl sodium eliminated butyric acid to give 1, 2, 3, 4, 5, 8- hexamethylnaphthalene(4). Bischloromethylation of 4, followed by lithium aluminum hydride reduction, gave 1. Octamethylnaphthalene gave 1, 4 adducts with maleic anhydride, ...

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