Products of the acid-catalyzed reaction of resorcinol with alpha,beta-
unsaturated ketones have been found to fall into two classes. The firs
t type of product is illustrated by 4-trimethyl-2H-1-benzopyran-2-yl)-
1,3-benzenediol, 1, formed in 91% yield by the reaction of resorcinol
with 4-methyl-3-penten-2-one (mesityl oxide). The second type of produ
ct is illustrated by (C-2-symmetric) 2,2'-spirobi(7-hydroxy-4,4-dimeth
ylchroman), 4, formed in 85% yield by the reaction of resorcinol with
2,6-dimethyl-2,5-heptadien-4-one (phorone). A number of examples of re
actions leading, in quite good yields, to products analogous to 1 are
presented, as well as some reactions that fail. Flavan 1 is identical
to the compound formed by the acid-catalyzed reaction of acetone with
excess resorcinol. Compound 1 and a steroidal analogue of 1 have been
found to be fluorescent.