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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 12
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Original Articles

Sulfuric Acid Catalyzed Decarbonylation of Alkoxyacetyl Chlorides

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Pages 1411-1414 | Published online: 19 Dec 2006

References

  • Summers , L. 1955 . Chem. Rev. , 55 : 301
  • Pascu , V. D. , Sava , L. , Gros , I. , Farcas , M and Craciun , V . 1983 . Chem. Abst. , 98 : 106797d
  • Ens , L. A. 1975 . Chem. Abst. , 83 : 27558p
  • Amato , J. S. , Karady , S. , Steizlnger , M. and Weinstock , L. M. 1979 . Synthesis , : 970
  • Stadlwieser , J . 1985 . Synthesis , : 490 Very recently Stadlwieser has reported the synthesis of chloromethyl methyl ether by the decarbonylation of methoxyacetyl chloride using aluminium chloride
  • Jones , M . 1984 . Synthesis , : 727 In 1984, Jones has reported the synthesis of chloromethyl methyl ether by the action of thionyl chloride on methoxyacetic acid
  • We have tried decarbonylation with TiCl4 and SnCl4 also. Sulfuric acid gives better results
  • Acid chlorides were obtained by the treatment of the corresponding acid with freshly distilled thionyl chloride. Alkoxyacetic acids (except methoxyacetic acid) were prepared by the reaction of the corresponding alcohols with ethyl bromoacetate in the presence of sodium hydride in THF, followed by hydrolysis
  • Pishnamazzade , V. F. and Gulieva , Sh.D. 1958 . Chem. Abst. , 52 : 1060h

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