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

HRID 2199074Notes

Reaction equation

HRID 2199074 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

Reactant 3

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 53664299HCID 53664299, compound

Product 1

HCID 30187552-Butenoic acid, 2,3,4,4-tetrachloro-, butyl esterYield 92%

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.

Workup

  1. temperatureheated
  2. stirringthe latter is agitated for 30 minutes at 80° C

Sources & evidence

ORD record
ord-e7e42fad9a484488b200bd9f0af02d11
Source dataset
uspto-grants-1982_11
Patent number
US04361686

Reaction notes

Loading…