Synthesis of 3- and 4-(ω-Phenylalkyl)catechols, the Sap Exuded from a Burmese Lac Tree, Melanorrhoea Usitate

Article abstract of DOI:10.1246/bcsj.64.1054

The presence of 3- and 4-(ω-phenylalkyl)catechols in Burmese lac has been confirmed by their synthesis. 3-(ω-Phenylalkyl)veratroles were synthesized by alkylation of ω-phenylalkyl bromide with aryl lithium derived from veratrole. 4-(ω-phenylalkyl)veratroles were similarly obtained from w-phenylalkyl bromide and 4-bromoveratrole.Demethylation of 3- and 4-(ω-phenylalkyl)veratroles with boron tribromide gave the corresponding catechols in good yields.