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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 5
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Original Articles

Improved Preparation of Methyl 3-Chloro-2-Butenoate; Precursor of the Wichterle Annulation Reagent, 1,3-Dichloro-2-Butene

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Pages 419-422 | Published online: 05 Dec 2006

References

  • Wichterle , O. , Prochazka , J. and Hofmann , J. 1948 . Coll. Czech. Chem. Commun. , 13 : 300
  • Hatch , L. F. and Perry , R. H. Jr. 1955 . J. Am. Chem. Soc. , 77 : 1136
  • Chalchat , J.-C. , Theron , F. and Vessière , R. 1972 . Ann. Chim. (Paris) , 7 : 269 Our stereochemical assignment follows that of. It is also consistent with the observation in ref. 2. that the E isomer is the lower boiling of the two
  • The crude mixture of chlorides may be purified by short-path (Kugelrohr) distillation before treatment with triethylamine, but an insignificant improvement in yield (to 43%) is thereby realized
  • The E, and Z, chloro esters may presumably be separated by careful fractionation (viz. ref. 2), but for the present purposes this was unnecessary
  • The crude reaction mixture contains a substantial amount of finely divided insoluble material, and emulsions are likely to form during the extractive workup. The layers separate satisfactorily upon standing

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