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Constituents of cannabis sativa L. An improved method for the synthesis of dl‐cannabichromene
Author(s) -
Eisohly Mahmoud A.,
Boeren Edward G.,
Turner Carlton E.
Publication year - 1978
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.5570150441
Subject(s) - chemistry , sodium borohydride , citral , silica gel , toluene , yield (engineering) , cannabis sativa , sodium hydroxide , chromatography , column chromatography , sodium , nuclear chemistry , butylamine , organic chemistry , catalysis , botany , materials science , amine gas treating , essential oil , metallurgy , biology
A new procedure was developed for the synthesis of cannabichromene (III) which involves reflux of equimolar amounts of olivetol (I), citral (II) and t ‐butylamine in toluene for 9 hours. The purification of III was best achieved by sodium borohydride reduction of unreacted II followed by column chromatography on 1% sodium hydroxide impregnated silica gel 60‐PF. The yield of III (62.0%) was much higher than that reported in the literature.