Potassium Hydroxide → 6,5'-Dimethylangelicin

Participants

Reaction Steps

To an ethanolic solution (100 ml) of 6-methyl-7-acetoxy-8-(2',3'-dibromopropyl) coumarin (XIII) (1.5 g) a volume of ethanolic 4% KOH solution was added, equivalent to a molar ratio coumarin/KOH 1:10. The mixture was refluxed for 80 min. in the dark, chilled, diluted with H2O (200 ml) and acidified with dil. HC1. The precipitate thus obtained was filtered, washed with H2O, dried and chromatographed on a silica gel column by eluting with CHC13, yielding the 6,5'-dimethylangelicin (XVI), crystallized from MeOH (0.52 g; m.p. 175-6° C.). ##STR22##

Provenance & Evidence