15582-49-7Relevant 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.
A NEW FORM OF THE REDUCTION OF BENZENE AND ITS ALKYL-SUBSTITUTRD DERIVATIVES TO 1,4-DIHYDRO DERIVATIVES IN THE LITHIUM-ISOPROPYL ALCOHOL-ETHYLENEDIAMINE SYSTEM
Bazyl'chik, V. V.,Fedorov, P. I.,Odinokov, V. N.
, p. 1668 - 1670 (2007/10/02)
A new method, convenient and effective for preparative purposes, is proposed for the reduction of benzene, toluene, and o-cymene in the lithium-isopropyl alcohol-ethylenediamine system.It is based on reaction at 85-95 deg C with arene, alcohol, diamine, and metal in molar equivalent ratios of 1:4-6:0.25-0.5:2-3.
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.