1-Butanol → 2,3,4,4-Tetrachloro-2-butenoic acid n-butyl ester
Reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[Cl:6][C:7](=[C:11]([Cl:15])[CH:12]([Cl:14])[Cl:13])[C:8](Cl)=[O:9].Cl>>[CH2:1]([O:5][C:8](=[O:9])[C:7]([Cl:6])=[C:11]([Cl:15])[CH:12]([Cl:14])[Cl:13])[CH2:2][CH2:3][CH3:4]Participants
4
Conditions
- Temperature
- 50 °C
Procedure
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.