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Preparation of ω‐hydroxynonanoic acid and its ester derivatives
Author(s) -
Kula Jozef,
Smigielski Krzysztof,
Quang Thuat B.,
Grzelak Iwona,
Sikora Magdalena
Publication year - 1999
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-999-0070-y
Subject(s) - chemistry , sodium borohydride , alkyl , methanol , acetic acid , boric acid , dehydrogenation , ozonolysis , organic chemistry , oleum , yield (engineering) , pyrolysis , sulfuric acid , nuclear chemistry , catalysis , materials science , metallurgy
Methyl ricinoleate was ozonized in methanol or in acetic acid and the intermediate hydroperoxides were reduced electrochemically on Pb‐cathode to give 9‐hydroxynonanoic acid 1 in high yields. The acid 1 was also prepared by direct castor oil ozonolysis in methanol followed by sodium borohydride reduction of the intermediate hydroperoxides. The cost of the electricity for the electroreduction was at least 30 times lower as compared with sodium borohydride consumption. 9‐Hydroxynonanoic acid was then transformed to alkyl 9‐acetoxynonanoates 3a–3d , for which 1 H nuclear magnetic reasonance, mass, and infrared spectra are given. Esterification of the hydroxy acid 1 with boric acid and pyrolysis of the resultant orthoborates produced 8‐nonenoic acid 4 in a 45% yield. Reaction of 4 with lower aliphatic alcohols in presence of Amberlyst 15 produced alkyl 8‐noneates 5a–5d along with some amounts of a cis/trans mixture of alkyl 7‐noneates.