✍ Scribed by Morr, Michael ;Wray, Victor ;Fortkamp, Jens ;Schmid, Rolf D.
No coin nor oath required. For personal study only.
(2__R__,4__R__,6__R__,8__R__)‐2,4,6,8‐Tetramethyldecanoic‐ and ‐undecanoic Acid of the Preen‐gland Wax from the Domestic Goose, Anser a.f. domesticus: Isolation, Synthesis of Derivatives and of the rac‐2,4,6,8‐Tetramethyldecanoic Acid
Large quantities of (2__R__,4__R__,6__R__,8__R__)‐2,4,6,8‐tetramethyldecanoic‐ and ‐undecanoic acid methyl ester (3 and 4) were obtained after transesterification and Spaltrohr^®^ distillation of the preen‐gland wax of the domestic goose. Hydrolysis with NaOH/dioxan afforded the acids 5 and 6. Reduction of 3 with LiAlH~4~ gave (2__R__,4__R__,6__R__,8__R__)‐2,4,6,8‐tetramethyldecanol (7). Esterification of 5 and 6 with octadecanol yielded the pure wax esters 1 and 2, while 5 with glycerol gave the triglyceride 9 and 5 with 7 afforded 8. Alcohol 7 and octadecyl bromide, in the presence of NaH/DMF, afforded the ether 10. The racemic acid 22, corresponding to 5, was obtained synthetically by starting with a modified Wittig reaction of 2‐(diethoxyphosphoryl)propionic acid ethyl ester on 2‐methylbutyraldehyde. Transesterification of the ethyl ester 21 with octadecanol gave the racemic wax ester 23, corresponding to 1. The optical activity and ^13^C data of the compounds are reported.
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