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Chemistry of acetals

Communication 2. Reaction of acetal with diketene and with acetoacetic ester

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Summary

  1. 1.

    The reaction of acetal with diketene in the presence of BF3 etherate gives as the main product 2-(1*-ethoxy) ethylacetoacetic ester (I). 1,1,3-Triethoxybutane (II) and 2-(1',3'-diethoxy) butylacetoacetic ester (III) are formed as by-products.

  2. 2.

    The reaction of acetal with acetoacetic ester was studied and found to give a good yield of 2-(1'-ethoxy) ethylacetoacetic ester (I).

  3. 3.

    On the example of acetaldehyde and crotonaldehyde acetals it was shown that acetals may be dimerized to compounds which could be of interest for the synthesis of polyene compounds.

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Literature cited

  1. 1.

    L. A. Yanovskaya, S. S. Yufit, and V. V. Kucherov, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 7, 1246 (1960).

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    Z. I. Torgashina and A. A. Naumchuk, Zhur. Obshchei Khim.,26, 3353 (1956). U. S. Pat. 2736741 (1956).

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    Federal German Republic Pat.849241 (1952); Chem. Zbl. 2992 (1953).

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    I. N. Nazarov, S. M. Makin, and B. K. Kruptsov, Doklady Akad. Nauk SSSR,122, 82 (1958).

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Yufit, S.S., Kucherov, V.F. Chemistry of acetals. Russ Chem Bull 9, 1538–1542 (1960). https://doi.org/10.1007/BF00909822

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Keywords

  • Acetal
  • Acetaldehyde
  • Ester
  • Good Yield
  • Main Product