Details

Autor(en) / Beteiligte

• Kunkuma, Vijaya Lakshmi
• Kaki, Shiva Shanker
• Rao, Bhamidipati V. S. K.
• Prasad, Rachapudi B. N.
• Prabhavathi Devi, Bethala L. A.

Titel

A simple and facile method for the synthesis of 1-octacosanol

Ist Teil von

• European journal of lipid science and technology, 2013-08, Vol.115 (8), p.921-927

Ort / Verlag

Weinheim: Blackwell Publishing Ltd

Erscheinungsjahr

2013

Quelle

Wiley-Blackwell Journals

Beschreibungen/Notizen

• An efficient synthetic method was developed for the preparation of 1‐octacosanol (C28‐alcohol) from commercially available lipid‐based intermediates namely sebacic acid (decanedioic acid) and stearyl alcohol. The key step in the synthesis is the preparation of tert‐butyl dimethyl octacos‐10‐enyloxy silane from 10‐tert‐butyl dimethyl silanyloxy decanal and octadecyl triphenylphosphonium bromide salt employing Witting reaction. This product on simultaneous hydrogenation of double bond and deprotection of tert‐butyldimethylsilyl protecting group in a single step on treatment with Pd/C and H2 in methanol at ambient temperature resulted octacosanol in 95% yields. The products were characterised by IR, 1H NMR, and GC–MS analysis. A simple and efficient synthetic method for the synthesis of 1‐octacosanol from commercially available sebacic acid and stearyl alcohol was developed. This study also resulted in an alternate application for sebacic acid which is being produced from agricultural feed stock castor oil.