p-Toluenesulfonic acid → 5-Hexadecene, 16,16-diethoxy-, (5Z)-

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Reaction Steps

The diethyl acetal or ketal is prepared by the above general procedure from (Z)-11-hexadecenal, (E)-and (Z)-citral in admixture and heptan-2-one using NH4Cl as catalyst in the first two cases and TsOH in the last. (Z)-1,1-Diethoxyhexadec-11-ene is obtained in 61.5% yield and has a b.p. 118°-120° C./0.05 mm, nD20 1.4475; (E)-o and (Z)-1,1-diethoxy-3,7-dimethoxyocta-2,6-diene in admixture are obtained in 83.6% yield and have b.p. 68°-70° C./0.2 mm, nD20 1.4511; 2,2-diethoxyheptane is obtained in 71% yield and has b.p. 88°-92° C./18 mm.

Provenance & Evidence