Camphor-10-sulfonic acid catalyzed condensation of 2-naphthol with aromatic/aliphatic aldehydes to 14-aryl/alkyl-14H-dibenzo(a,j)xanthenes
2014
(±)-Camphor-10-sulfonic acid (CSA) catalyzed condensation of 2-naphthol with
both aliphatic/aromatic aldehydes at 80°C yielded
14-alkyl/aryl-dibenzoxanthenes as the sole product in high yields. However,
the same condensation with benzaldehyde at 25°C afforded a mixture of
intermediate 1,1-bis-(2-hydroxynaphthyl)phenylmethane and
14-phenyl-dibenzoxanthene while the condensation with aliphatic aldehydes at
25°C furnished the corresponding 14-alkyl-dibenzoxanthenes as the sole
product. Moreover, condensation of 2-naphthol with aromatic/aliphatic
aldehydes with low catalyst loading (2 mol%) was greatly accelerated under
microwave irradiation to afford the corresponding
14-aryl/alkyl-dibenzoxanthenes as the sole product in high yields.
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