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Synthesis of 5‐phenylnaphtho[1,2‐ b ]benzofuran by ambident alkylation of 1‐naphthol
Author(s) -
Campaigne E.,
Weddleton Richard F.
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230604
Subject(s) - chemistry , alkylation , benzofuran , dehydrogenation , medicinal chemistry , alcohol , ether , organic chemistry , catalysis
Reaction of 1‐naphthol with 2‐chlorocyclohexanone in alkaline alcohol gave as the major product 5‐(2′‐oxocyclohexyl)‐7,8,9,10‐tetrahydronaphtho[1,2‐ b ]benzofuran ( 1 ), which could be converted to the title compound 5 by reduction and dehydrogenation. This product arises from ambident alkylation of 1‐naphthol at the 2‐and 4‐positions. Via the 2′‐oxocyclohexyl ether, 5 was also synthesized from 4‐phenyl‐1‐naphthol.