Reaktion #78329

Reaktionsgleichung

2-(chloromethyl)-acrylonitrile

2-hydroxyethylphosphonic acid dimethylester

triethylamine

TEA

2-(chloromethyl)-acrylonitrile

→

colourless liquid

Ausbeute 54.2%

2-[4-(dimethoxyphosphoryl)-2-oxabutyl]-acrylonitrile

Ausbeute 54.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux
2. 2
   Temperaturis heated for a further 24 hours
3. 3
   Temperaturunder reflux
4. 4
   TemperaturAfter the reaction mixture has cooled
5. 5
   Filtrationthe formed deposit of TEA hydrochloride is filtered out and
6. 6
   Waschenis washed twice with 50 ml THF
7. 7
   EinengenAfter the THF phases have been concentrated on the rotary evaporator
8. 8
   Waschenwashed twice with water
9. 9
   TrocknenAfter it has been dried over anhydrous sodium sulphate
10. 10
    Einengenthe mixture is concentrated
11. 11
    workup.DISTILLATIONdistillation in the fine vacuum

Vorschrift

86.3 g (850 mmol) 2-(chloromethyl)-acrylonitrile are added dropwise at room temperature to a solution of 130.9 g (850 mmol) 2-hydroxyethylphosphonic acid dimethylester, 85.9 g (850 mmol) triethylamine (TEA) and 40 mg phenothiazine (stabilizer) in 1 l THF. Subsequently, the mixture is heated for 6 hours at 65° C. under reflux. 9.1 g (90 mmol) TEA and 9.1 g (90 mmol) 2-(chloromethyl)-acrylonitrile are once again added one after the other and the mixture is heated for a further 24 hours under reflux. After the reaction mixture has cooled, the formed deposit of TEA hydrochloride is filtered out and is washed twice with 50 ml THF. After the THF phases have been concentrated on the rotary evaporator, the residual raw product is taken up in 650 ml methylene chloride and washed twice with water. After it has been dried over anhydrous sodium sulphate, the mixture is concentrated and the residual liquid undergoes fractional distillation in the fine vacuum. 101.0 g (54% yield) of a colourless liquid results at b.p. 150° C. (0.05 mbar).

Quelle