تفاعل #62751

معادلة التفاعل

cyclohexanone

n-Butyl lithium

hexane

p-Methoxyphenylacetonitrile

ammonium chloride

→

1-[Cyano(-methoxyphenyl)methyl]cyclohexanol

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe temperature was maintained below -50° C.
2. 2
   workup.ADDITIONAfter the addition
3. 3
   درجة الحرارةthe reaction mixture was maintained below -50° C. for 30 minutes
4. 4
   أخرىto rise to 0° C.
5. 5
   أخرىThe layers were separated
6. 6
   استخلاصthe aqueous layer extracted with diethyl ether
7. 7
   غسيلThe combined organic solution was washed with brine
8. 8
   تجفيفdried over magnesium sulphate
9. 9
   أخرىevaporated
10. 10
    أخرىThe product crystallized (25.2 gm, m.p. 125°-127° C.)

الإجراء التجريبي

p-Methoxyphenylacetonitrile (50 gm, 0.3 mole) was added to dry tetrahydrofuran (250 ml) and the solution cooled to -70° C. under nitrogen. n-Butyl lithium in hexane 210 ml, 0.3 mole) was added dropwise, with stirring. The temperature was maintained below -50° C. and a yellow precipitate appeared. After the addition was complete, the reaction mixture was maintained below -50° C. for 30 minutes and cyclohexanone (35 ml, 0.3 mole) was added. After a further 45 minutes below -50° C. the temperature was allowed to rise to 0° C. and a saturaged ammonium chloride solution was added. The layers were separated and the aqueous layer extracted with diethyl ether. The combined organic solution was washed with brine, dried over magnesium sulphate and evaporated. The product crystallized (25.2 gm, m.p. 125°-127° C.).

المصدر