15582-48-6Relevant articles and documents
Compounds of the menthane series. Synthesis of unsaturated primary alcohols with the o- and p-menthane skeletons
Fedorov,Fedorova,Sheverdov,Pavlov,Eremkin
, p. 806 - 812 (2016/07/30)
Precursors to terpene alcohols of the o- and p-menthane series (o-cimen-7-ol and o- and p-cimen-9-ols) were synthesized, and their reduction with lithium in ethylenediamine was studied. The reduction of o- and p-cimen-9-ols in the presence of isopropyl alcohol selectively afforded the corresponding 1,4-dihydro derivatives. Under analogous conditions, o-cimen-7-ol was converted into a mixture of unsaturated hydrocarbons. The reduction with lithium in ethylenediamine in the absence of isopropyl alcohol in all cases gave mixtures of menthene alcohols.
STUDIES OF COMPOUNDS IN THE MENTHANE SERIES. XIX. SYNTHESIS AND PROPERTIES OF TRANS-o-4-MENTHEN-8-OL AND STEREOISOMERIC o-5-METHEN-8-OLS
Bazyl'chik, V. V.,Fedorov, P. I.,Klyuev, N. A.,Dank, E. Kh.
, p. 1320 - 1327 (2007/10/02)
Trans-o-4-Menthen-8-ol and cis- and trans-o-5-menthen-8-ols have been prepared via the Diels-Alder reactions of 1,3-butadiene with crotonaldehyde in the presence of boron trifluoride etherate, and piperylene with methyl acrylate, respectively.The dehydration reactions of these alcohols have been studied in the presence of acetic anhydride and potassium bisulfate; the latter reagent demonstrates a high reaction selectivity.
INVESTIGATION OF COMPOUNDS IN THE o-MENTHANE SERIES XI. ISOMERIZATION TRANSFORMATIONS OF o-1,4-MENTHADIENES
Bazyl'chik, V. V.,Fedorov, P. I.
, p. 1221 - 1227 (2007/10/02)
Under the conditions of base catalysis under the influence of potassium tert-butoxide in dimethyl sulfoxide and lithium and calcium amides o-1,4-menthadiene forms equilibrium mixtures of o-1,3-menthadiene, o-1,5-menthadiene, and the skeletal rearrangement product 1-isopropyl-5-ethylidenecyclopentene.In the presence of NaX and KX zeolites competing dehydrogenation and disproportionation of the hydrogen occur in o-1,4-menthadiene with the formation of a mixture of o-menthenes and o-cymene.With increase in temperature the dehydration process becomes determining.With acid catalysis the transformation of o-1,4-menthadiene into 1-isopropyl-5-ethylidenecyclopentene and dehydration to o-cymene are the mainpaths.