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Synthesis of mannich bases of bioactive benzylphenols
Author(s) -
Jurd Leonard
Publication year - 1984
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.5570210118
Subject(s) - chemistry , phenol , mannich reaction , mannich base , methanol , toluene , boiling , organic chemistry , phenols , quinone , quinone methide , formaldehyde , catalysis
Abstract 2,4‐Bis(1,1‐dimethyl)‐6‐[(4‐methoxyphenyl)methoxymethyl]phenol ( 4 ), prepared by oxidation of 2,4‐bis(1,1‐dimethylethyl)‐6‐[(4‐methoxyphenyl)methyl]phenol ( 1 ) with silver oxide in methanol, reacts with secondary amines in boiling toluene to give Mannich bases ( 6 ) related to the biologically active o ‐benzylphenol. Mannich basis of the isomeric p ‐benzylphenol ( 7 ) were prepared by reaction of amines with the p ‐quinone methide formed by oxidation of 7 .