Reaction #62751

Reaction equation

cyclohexanone

n-Butyl lithium

hexane

p-Methoxyphenylacetonitrile

ammonium chloride

→

1-[Cyano(-methoxyphenyl)methyl]cyclohexanol

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureThe temperature was maintained below -50° C.
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Temperaturethe reaction mixture was maintained below -50° C. for 30 minutes
4. 4
   Otherto rise to 0° C.
5. 5
   OtherThe layers were separated
6. 6
   Extractionthe aqueous layer extracted with diethyl ether
7. 7
   WashThe combined organic solution was washed with brine
8. 8
   Dryingdried over magnesium sulphate
9. 9
   Otherevaporated
10. 10
    OtherThe product crystallized (25.2 gm, m.p. 125°-127° C.)

Procedure

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.).

Source