Synthesis and Identification of ω-Phenylalkylcatechols in Burmese Lac

Abstract

The presence of 3-(10′-phenyldecyl)-(2) (2%), 3-(12′-phenyldodecyl)- (3) (6%), 4-(10′-phenyldecyl)-(4) (0.3%) and 4-(12′-phenyldodecyl)- benzene-1,2-diol (5) (0.3%) in Burmese lac , the sap of Melanorrhoea usitata Wall has been confirmed by the synthesis of these compounds and a comparison of the gas chromatographic retention times and the mass spectral characteristics of their bis-O-( trimethylsilyl ) derivatives with the derivatives of the natural products. Typically, 3,4- bis ( benzyloxy ) benzaldehyde (7) on Wittig reaction with triphenyl (11- phenylundecyl ) phosphonium bromide (20) and subsequent catalytic hydrogenation of the resultant olefin gave compound (5) in 59% overall yield.