Conclusions
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1.
The reaction of limonene oxide with ethanol in both alkaline and acid media proceeds stereospecifically with the formation: a) in alkaline medium of (−)-2-hydroxy-1-ethoxy-trans-p-menth-8-ene and the steric isomers of (−)-1-hydroxy-2-ethoxy-trans-p-menth-8-ene and (+)-1-hydroxy-2-ethoxy-cis-p-menth-8-ene; b) in acid medium of (−)-1-hydroxy-2-ethoxy-trans-p-menth-8-ene and the steric isomers of (−)-2-hydroxy-1-ethoxy-trans-p-menth-8-ene and (+)-2-hydroxy-1-ethoxy-cis-p-menth-8-ene. The isomerization products of limonene oxide: dihydrocarvone, trans-carveol and trans-isocarveol, are also formed in alkaline medium.
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2.
The NMR method was used to study the conformation of the obtained addition products of ethanol to limonene oxide.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1061–1067, May, 1973.
The GLC analysis was run by A. A. Martynov, for which the authors express their gratitude to him.
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Mukhamedova, L.A., Kudryavtseva, M.I., Shagidullin, R.R. et al. Formation of steric isomers in reaction of limonene oxide with ethanol. Russ Chem Bull 22, 1020–1025 (1973). https://doi.org/10.1007/BF00854241
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DOI: https://doi.org/10.1007/BF00854241