Vanillin production association

CgHeOa. White crystals m.p. 37°C, b.p. 263°C. Occurs associated with vanillin. Obtained on oxidation of various natural products such as piperine. Used extensively in soap perfumery. 

Pavolini (118) who prepared curcumin by condensation of acetylacetone with vanilline. He observed that Knoevenagel condensation, one of the main side reactions, could be suppressed by adding boric oxide. This method was further developed by Pabon (119) who first prepared a complex from acetylacetone and boric anhydride and reacted the product with vanilline in the presence of triisopropyl borate and butylamine. Yields calculated on vanilline were thus improved from 10% to 80%. Besides several other indutrial applications (120-123) the method was also used for the synthesis of dihydroyashabushiketol (6) (11) and the tetramethylether of oregonin (11) (14). By selective alkylation of acetylacetone at C-3 Pedersen and associates exploited the above method for the preparation of a series of non-natural diaiylheptanoids substituted at C-4 (124). 

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