Plant components. XII. Acid-catalyzed conversions of monoterpenes was written by Geyer, Sigrid;Zieger, Werner;Mayer, Roland. And the article was included in Zeitschrift fuer Chemie in 1966.Application of 2451-01-6 This article mentions the following:
Reactions of monoterpenes with acidic dehydrating reagents were reexamined and the qual. and the approx. quant. composition of the reaction products was determined by distillation, gas chromatog., spectroscopy, and thin-layer chromatog. All these reactions were assumed to proceed by the formation of different C10 carbonium ions. Hydration occurred under mild conditions and dehydration and isomerization under more severe conditions. The most stable compounds were α-terpinene (I), isoterpinolene (II), and p-cymene (III). When an endocyclic or exocyclic double bond could arise from proton splitting, the endocyclic double bond was predominant in the 6-membered ring and the exocyclic double bond in the 5-membered ring. Transition of acyclic and bicyclic to monocyclic compounds occurred readily, but the opposite transition was not observed The following compounds were formed on treating the different monoterpenes with 10% (A), 30% (B), and 50% H2SO4 (C), 10% (D), 30% (E), and 50% H3PO4 (F) at different temperatures: Dipentene (IIIa) gave no reaction with A, B, and C at 20°, but at 60° 5% I, and 5% terpinolene (IV) + II were formed with B, and 10% I, 10% γ-terpinene (V) + III, and 10% II formed with C. At 100° were formed I 10, V + III 10, IV + II 10%, and traces of 1,8-cineole (VI) (?) with A; I 20, V + III 25, and II 10% with B; I 30, V + III 25, IV 5, and II 15% with C. Reaction of V with F at 100° gave I 10, III 10, II 5%, and traces of IV. α-Terpineol gave terpin hydrate (VII) 8, IIIa 5, I 15, V 10, III 25, II 5, and VI 25% with C at 20°, β-terpineol gave IIIa 10, I 30, V 15, III 15, IV 10, II 20%, and traces of p-menthane and p-mentha-3,8(9)-diene at 60° with C. Reaction of VII with E at 100° gave IIIa 15, I 15, V + III 30, IV 15, II 5, and VI 15%. Tables for reaction conditions and products formed from camphene, camphene hydrate, methylcamphenilol, α-pinene, borneol, isoborneol, and α-fenchol with A-E were given. In the experiment, the researchers used many compounds, for example, rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate (cas: 2451-01-6Application of 2451-01-6).
rel-(1s,4s)-4-(2-Hydroxypropan-2-yl)-1-methylcyclohexanol hydrate (cas: 2451-01-6) belongs to alcohols. Because alcohols are easily synthesized and easily transformed into other compounds, they serve as important intermediates in organic synthesis. Grignard and organolithium reagents are powerful tools for organic synthesis, and the most common products of their reactions are alcohols.Application of 2451-01-6
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts