Conclusions
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1.
Limonene dioxide in the presence of BF3·O(C2H5)2, under mild conditions, undergoes opening of the 1,2-epoxy ring with the formation of (−)-2-hydroxy-l-ethoxy-8,9-epoxy-trans-p-menthane (+)-2-hydroxy-l-ethoxy-8,9-epoxy-cis-p-menthane, and (−)-1-hydroxy-2-ethoxy-8,9-epoxy-trans-p-menthane. The direction of the reaction is determined by conformational and electronic factors.
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2.
In the presence of NaOC2H5 the 8,9-epoxy ring is opened with the formation of (−)-8-hydroxy-9-ethoxy-1,2-epoxy-trans-p-menthane and (+)-8-hydroxy-9-ethoxy-1,2-epoxy-cis-p-menthane.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 404–407, February, 1974.
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Mukhamedova, L.A., Kudryavtseva, M.I. & Martynov, A.A. Reaction of limonene dioxide with ethanol. Russ Chem Bull 23, 370–373 (1974). https://doi.org/10.1007/BF00924690
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DOI: https://doi.org/10.1007/BF00924690