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An Efficient Synthesis of 5,6‐Dimethoxy 1‐ and 2‐Naphthols via Teuber Reaction
Author(s) -
Cui Jiahua,
Li Shaoshun
Publication year - 2013
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201300065
Subject(s) - chemistry , yield (engineering) , 1 naphthol , formate , 2 naphthol , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
Based on the oxidation of 1,5‐naphthalenediol ( 4 ) and 6‐bromo‐2‐naphthol ( 9 ) via Teuber reaction, an efficient synthesis of 5,6‐dimethoxy‐1‐naphthol ( 1 ) and 5,6‐dimethoxy‐2‐naphthol ( 2 ) was achieved with high overall yield (16% for 1 and 25% for 2 ). The key steps of the synthetic strategy involved the oxidation of naphthols ( 4 and 9 ) to the corresponding naphthoquinones ( 5 and 10 ) and the conversion of 5,6‐dimethoxy‐2‐naphthaldehyde to 5,6‐dimethoxy‐2‐naphthol formate through Baeyer‐Villiger oxidation‐rearrangement.