Reaction #2146730

Reaction equation

cyclohexanone

HCl

tert-butyllithium

pentane

isobutyl iodide

→

1-isobutylcyclohexanol

Solvents

diethyl ether

Conditions

Workup

1. 1
   Temperaturewarmed to 10° C.
2. 2
   Temperaturecooled to −70° C.
3. 3
   workup.ADDITIONAt the end of the addition
4. 4
   Otherto reach room temperature
5. 5
   ExtractionThe water phase was extracted with diethyl ether (300 ml)
6. 6
   Washthe combined organic phases were washed with water (400 ml) and aqueous saturated NaCl solution (500 ml)
7. 7
   Dryingdried (50 g MgSO4)
8. 8
   Otherthe solvent evaporated

Procedure

At −60° C., a solution of 1.7M tert-butyllithium in pentane (1000 ml, 1.7 mol, 2.1 eq.) in diethyl ether (800 ml) was treated dropwise within 1 h with isobutyl iodide (157 g, 0.81 mol, 1.0 eq.). The resulting solution was stirred at −70° C. for 45 min., warmed to 10° C., cooled to −70° C., and treated at this temperature within 4 h with cyclohexanone (100.7 ml, 0.971 mol, 1.2 eq.). At the end of the addition, the reaction mixture was allowed to reach room temperature before being poured into ice/H2O (500 ml) and acidified with concentrated HCl. The water phase was extracted with diethyl ether (300 ml) and the combined organic phases were washed with water (400 ml) and aqueous saturated NaCl solution (500 ml), dried (50 g MgSO4) and the solvent evaporated to give the crude 1-isobutylcyclohexanol (148 g).

Source