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Study of halogenation of 3-hydroxymethylcyclohexene

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The reaction of cyclohexene, formaldehyde, and hydrochloric acid at a temperature of 20-30°C leads to the formation of di(trans-2-chlorocyclohexylmethyl)formal.

  2. 2.

    3-Hydroxymethylcyclohexene, formed during the dehydrochlorination of di(trans-2-chlorocyclohexylmethyl)formal by the action of alcoholic alkali, followed by methanolysis of dehydrochlorination of trans-1-hydroxymethyl-2-chlorocyclohexane by the action of potassium acetate, is converted into 3-chloro(bromo)methylcyclohexene via a tosylate, by the action of calcium chloride (sodium bromide) in glycerin.

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Authors and Affiliations

  1. The A. V. Topchiev Institute of Petrochemical Synthesis, Academy of Sciences of the USSR, Moscow

    N. P. Volynskii, L. A. Zegel'man & G. N. Gordadze

Authors
  1. N. P. Volynskii
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  2. L. A. Zegel'man
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  3. G. N. Gordadze
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No, 12, pp. 2805–2809, December, 1987.

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Volynskii, N.P., Zegel'man, L.A. & Gordadze, G.N. Study of halogenation of 3-hydroxymethylcyclohexene. Russ Chem Bull 36, 2601–2605 (1987). https://doi.org/10.1007/BF00957243

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  • DOI: https://doi.org/10.1007/BF00957243

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