Conclusions
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1.
Optically active and racemic menthyl furoates were produced for the first time, and their constants were determined.
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2.
The kinetics of the hydrogenation of menthyl furoate on a Pd(OH)2/C catalyst was investigated. Hydrogenation leads primarily to the tetrahydro-product without intermediate formation of the di-hydro-product. The activation energy of the process is equal to 4.9 kcal/mole.
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3.
Asymmetrical synthesis was carried out in the furan series: it was shown that hydrogenation proceeds stereospecifically. The optical yield of tetrahydrofuryl alcohol is 20%.
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E. I. Klabunovskii, L. F. Godunova, R. A. Karakhanov, E. Yu. Beilinson, T. G. Rybina, and I. A. Rubtsov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1 (1969).
R. G. Hiskey and R. G. Northrop, J. Amer. Chem. Soc.,83, 4798 (1961).
L. F. Godunova, E. I. Klabunovskii, and A. A. Balandin, Izv. Akad. Nauk SSSR, Ser. Khim., 1593 (1968).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 303–307, February, 1969.
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Godunova, L.F., Klabunovskii, E.I., Karakhanov, R.A. et al. Hydrogenation of optically active esters of furancarboxylic acid. Russ Chem Bull 18, 259–262 (1969). https://doi.org/10.1007/BF00905531
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DOI: https://doi.org/10.1007/BF00905531