74285-75-9Relevant academic research and scientific papers
SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS. L. SYNTHESIS OF THE NITRILES AND HYDROXYNITRILES OF RETINOIC ACID
Zakharova, N. I.,Gutnikova, N. P.,Bekker, A. R.,Filippova, T. M.,Miropol'skaya, M. A.,Samokhvalov, G. I.
, p. 1870 - 1874 (2007/10/02)
Glycidonitrile was synthesized from 9-methyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-9,11-octadien-13-one and chloroacetonitrile by a modified Darzens reaction.Opening of the epoxide ring in the glycidonitrile gave 9,14-dihydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-10,12-nonadiene-15-nitrile with a yield of 70percent calculated on the ketone.Partial dehydration of the latter gave 14-hydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-8,10,12-nonatriene-15-nitrile - the key compound in the synthesis of the biologically active analog of the vitamin Ametabolite.The total dehydration of the dihydroxynitrile led to retinonitrile.
