Abstract
Relationship between the yield and the heating time, kinds of bases used, and its amount, during the preparation of coumarin-3-carboxylic acid by the condensation of salicylaldehyde and malonic acid were examined and the results obtained are shown in Tables II and III. It was thereby found that (1) the starting material should be mixed while hot, (2) as for the kind and amount of the base used, the yield was better when the ratio of salicylaldehyde: malonic acid: base was 1:2:1 with primary bases and 1:1:2 with secondary bases, while the yield was invariably poor with tertiary bases, and (3) aniline proved to be the best of the bases used on the yield. From the reaction of 2-hydroxybenzylidene-aniline, -p-toluidine, and -bispiperidine, this condensation reaction was found to require a 2-hydroxybenzylidene base as the intermediate.
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