تفاعل #654832

معادلة التفاعل

8-methyl-8-methoxycarbonyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene

hydrochloric acid

potassium hydroxide

lithium aluminum hydride

→

white solid

المردود 82.4%

8-methyl-8-hydroxymethyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene

المردود 82.4%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added from a dripping funnel over one hour
2. 2
   أخرىfollowed by a reaction for 2.5 hours at 70° C
3. 3
   درجة الحرارةto cool to room temperature
4. 4
   استخلاصThe reaction solution was then extracted with toluene
5. 5
   غسيلThe salt-out product was washed several times with water
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   أخرىToluene was evaporated

الإجراء التجريبي

37.6 g of lithium aluminum hydride and 800 ml of tetrahydrofuran were added to a flask and maintained at 0° C. in a nitrogen atmosphere. Then, 200 g of 8-methyl-8-methoxycarbonyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene dissolved in 200 ml of tetrahydrofuran was added from a dripping funnel over one hour, followed by a reaction for 2.5 hours at 70° C. The reaction solution was allowed to cool to room temperature and a 10% aqueous solution of potassium hydroxide was added gradually, followed by further addition of 10% aqueous solution of hydrochloric acid. The reaction solution was then extracted with toluene and the reaction product was salted out from saturated brine. The salt-out product was washed several times with water and dried over anhydrous magnesium sulfate. Toluene was evaporated to obtain 145 g of a white solid of 8-methyl-8-hydroxymethyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene shown by the following formula (19).

المصدر