Studies in the Synthesis of Coumarino-α-pyrones and Furocoumarins; Part XIX*. Synthesis of 4-Hydroxy-3-phenyl-5', 8-dimethylpsoralene.

Chemistry Department, Faculty of Science, M. S. University of Baroda, Baroda. Manuscript received 5 July 1972 ; revised 10 September 1974 ; accepted 12 September 1974 2,4-Dihydroxy-3-methyl-ω-phenyl acetophenone on allylation gave 4-allyloxy derivative, which on condensation with diethyl carbonate furnished 4-hydroxy-3-phenyl-7-allyloxy-8-methylcoumarin (Ia). Methylation, followed by Claisen rearrangement of (Ia) gave the corresponding 6-allyl compound, which on cyclisation followed by dehydrogenation gave 4-methoxy- and 4-hydroxy-3- phenyl-5', 8-dimethylpsoralene