Verfahren zur Herstellung von in 2-Stellung substituierten Resorcinderivaten

摘要

1,181,415. 2-Substituted resorcinol derivatives. A. ESCHENMOSER, and T. PETRZILKA. 3 Nov., 1967 [4 Nov., 1966], No. 50015/67. Heading C2C. A process for the manufacture of 2-substituted resorcinol derivatives of the general formula where R represents a carboxyl or carbalkoxy group, R1 represents an alkyl group, R2 represents an alkyl group and R3 and R4 each represent an alkyl, alkenyl or alkynyl group or two of the symbols R2, R3 or R4 are linked together to form a 5- or 6-membered ring and wherein the broken lines denote that the substituents attached thereby are optional comprises condensing a 2-unsubstituted resorcinol of the general formula where R and R1 and the broken lines have the significance given above with an unsaturated alcohol of the general formula where R2, R3 and R4 have the significance given above in the presence of an N,N-dimethylformamide dialkyl acetal. In examples resorcinol is condensed with linalool, olinetol with (+)- trans-p-menthadien-(2,8)-ol-1 and 6-carbethoxyolinetol is condensed with ( + )-cis- and -trans-pmenthadien-(2,8)-ol-(1) in the presence of N,N- dimethyl-formamide dineopentyl acetal. The products are stated to be cyclized by known methods to yield benzopyran or benzofuran derivatives. Among the products are cannabidiolcarboxylic acid ethyl ester and cis- and trans-cannabidiol.