Phenol sulfate esters: ultraviolet, infrared, 1H and 13C nuclear magnetic resonance spectroscopic investigation

Abstract

Renewed interest in naturally occurring phenol sulfate ester salts has necessitated modem spectroscopic investigation of these compounds. Synthetic methods, plus spectroscopic (uv, ir, 1H nmr, 13C nmr), chromatographic, and electrophoretic properties are given for the potassium salts of phenyl sulfate (1), pyrocatechol disulfate (2), resorcinol disulfate (3), hydroquinone disulfate (4), phloroglucinol mono- (5), di- (6), and tri- (7) sulfates, and for the 2-sulfate (8) and 2,5-disulfate (9) of 1,2,3,5-tetrahydroxybenzene (10). 13C nmr chemical shift effects resulting from the replacement of phenolic —OH with —OSO3K are reported. Spectroscopic properties of the related compounds 1,2,3-tribenzyloxybenzene (11), 2,6-dibenzyloxy-1,4-benzoquinone (12), 2,6-dimethoxy-1,4-benzoquinone (13), 1,3-dibenzyloxy-2,5-dihydroxybenzene (14), and of a tentatively identified 1,3-dibenzyloxy-2,5-dihydroxybenzene monoethyl ether (15) are available as supplementary material.