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Synthesis of α-chloro carboxylic acids by addition of chlorine in a formic acid medium to compounds containing a CCl2=CH group

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Summary

  1. 1.

    Reaction of chlorine with compounds containing the CCl2=CH group in a medium of anhydrous formic acid followed by treatment with water gives α -chloro carboyxlic acids in good yields.

  2. 2.

    In this way, from 1,1,3-trichloropropene, l,l-dichloro-3-methoxypropene, 3,3-dichloroallyl formate, 1,1,5-trichloro-1-pentene, 5,5-dichloro-4-pentenyl formate, 1,1,7-trichloro-1-heptene, and 1,1,9-trichloro-1-nonene the following α-chloro carboxylic acids were prepared: 2,3-dichloro- and 2-chloro-3-methoxy-propionic acids, 2-chlorohydracrylic acid formic ester, 2,5-dichlorovaleric acid, 2-chloro-5-hydroxyvaleric acid formic ester, 2,7-dichloroheptanoic acid, and 2,9-dichlorononanoic acid.

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Literature cited

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    A. N. Nesmeyanov, V. N. Kost, and R. Kh. Freidlina, Doklady Akad. Nauk SSSR 103, 1029 (1955).

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    R. Kh. Freidlina, V. N. Kost, and A. N. Nesmeyanov, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk 1956, 1202.

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    A. N. Nesmeyanov, V. N. Kost, T. T. Vasil'eva, and R. Kh. Freidlina, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk 1958, 152.

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    A. N. Nesmeyanov, R. Kh. Freidlina, and R. G. Petrova, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk 1957, 451.

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Kost, V.N., Sidorova, T.T., Freidlina, R.K. et al. Synthesis of α-chloro carboxylic acids by addition of chlorine in a formic acid medium to compounds containing a CCl2=CH group. Russ Chem Bull 8, 2025–2027 (1959). https://doi.org/10.1007/BF00909044

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Keywords

  • Ester
  • Chlorine
  • Formic Acid
  • Carboxylic Acid
  • Chloro