Reacción #642972

Ecuación de reacción

4-vinyl-1-cyclohexene-1,2-epoxide

suberic acid

triethylamine

→

Bis(2-hydroxy-5-vinyl-cyclohexyl)Suberate

Rendimiento 22.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroequipped with a stir bar, water condenser
2. 2
   Otrodrying tube
3. 3
   workup.ADDITIONCuprous chloride and 2,5-diphenylbenzoquinone (200-500 ppm) were added
4. 4
   Otropolymerization
5. 5
   LavadoThe reaction mixture was washed twice with 2N HCl and twice with 2N NaOH (100 ml each washing)
6. 6
   SecadoThe organic layer was then dried with magnesium sulfate
7. 7
   Otrothe toluene removed by flash evaporation
8. 8
   Otroto remove the last traces of toluene
9. 9
   workup.DISTILLATIONby azetropic distillation
10. 10
    Otrofor several hours
11. 11
    Temperaturawith gentle heating at 50° C
12. 12
    OtroA brown viscous oil, 6.4 g (22% yield) was obtained

Procedimiento

As shown in scheme 1, the reagents, 4-vinyl-1-cyclohexene-1,2-epoxide (12.4 g, 0.1 moles), suberic acid (13.7 g, 0.07 moles), triethylamine (15.9 g, 0.016 moles) and toluene (60 mL) were combined in a reaction flask equipped with a stir bar, water condenser and drying tube. Cuprous chloride and 2,5-diphenylbenzoquinone (200-500 ppm) were added to inhibit polymerization. The temperature of the reaction flask was controlled with a thermal heating unit. The reaction mixture was heated to 90° C., and the progress of the reaction monitored by gas chromatography (GC). After about 5 hours the epoxide could not be detected by GC analysis. The reaction mixture was washed twice with 2N HCl and twice with 2N NaOH (100 ml each washing). The organic layer was then dried with magnesium sulfate and the toluene removed by flash evaporation. Methanol was used to remove the last traces of toluene by azetropic distillation. A vacuum was applied to the distilled product (pressure less than one mm for several hours with gentle heating at 50° C. A brown viscous oil, 6.4 g (22% yield) was obtained. The product was analyzed by electo-spray time of flight mass spectroscopy (M+H and M+Na fragments).

Fuente