1-Butanol → 2-Butenoic acid, 2,3,4,4-tetrachloro-, butyl ester

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Reaction Conditions

Reaction Steps

An agitated flask is charged with 0.5 mole of n-butanol and heated under stirring to 50° C. Within 30 minutes, 60.6 g (0.25 mol) of 2,3,4,4-tetrachloro-2-butenoic acid chloride is added dropwise to the charge, and the latter is agitated for 30 minutes at 80° C. During this step the main quantity of the thus-formed hydrogen chloride is driven off in the gaseous phase. Subsequently, the reaction mixture is fractionated without neutralization over a 10 cm column under vacuum, thus obtaining 64.4 g (0.23 mol) of 2,3,4,4-tetrachloro-2-butenoic acid n-butyl ester; b.p. 95° C./0.6 mbar; nD20 --1.5050. Yield: 92% of theory.

Provenance & Evidence