تفاعل #642972

معادلة التفاعل

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

suberic acid

triethylamine

→

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

المردود 22.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىequipped with a stir bar, water condenser
2. 2
   أخرىdrying tube
3. 3
   workup.ADDITIONCuprous chloride and 2,5-diphenylbenzoquinone (200-500 ppm) were added
4. 4
   أخرىpolymerization
5. 5
   غسيلThe reaction mixture was washed twice with 2N HCl and twice with 2N NaOH (100 ml each washing)
6. 6
   تجفيفThe organic layer was then dried with magnesium sulfate
7. 7
   أخرىthe toluene removed by flash evaporation
8. 8
   أخرىto remove the last traces of toluene
9. 9
   workup.DISTILLATIONby azetropic distillation
10. 10
    أخرىfor several hours
11. 11
    درجة الحرارةwith gentle heating at 50° C
12. 12
    أخرىA brown viscous oil, 6.4 g (22% yield) was obtained

الإجراء التجريبي

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).

المصدر