water and 10 ml. of 2 IV hydrochloric acid. The solution was stirred in the cold for 30 min. and then 1.06 g. of benzaldehyde was added. After 10 min. stirring at room temperature, solid began to appear in the mixture. The beige-colored solid was separated after 2 hr. yielding 2.15 g. (47.3%) of product melting at 107-111°with considerable bubbling. The product was purified by dissolving in cold ethanol and precipitating by the addition of water to yield a straw-colored solid, m.p. 109-111°d ec.
The lithium a l u~n i n u~n hydride reduction of nitriles in the aroxnatic resin acid series to aldimines and the conversion of the products to other derivatives are described. The effect of the stereochemistry of the nitriles on the rate of reduction is noted. The transformation of dehydroabietane into a dehydro product is indicated. The syntheses of a desoxydecarboxy-5,6-dehydro-7-keto derivative of podocarpic acid and its optical antipode are discussed. The stereochemistry of hydrogenation of 5,6-dehydro derivatives of podocarpic acid is reported. The effect of a 7-keto group on the rate of hydrolysis of methyl esters of aromatic resin acids is illustrated. The reactions of 6-bromo-7-keto derivatives of methyl podocarpate with bases are portrayed.
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