Welcome to LookChem.com Sign In | Join Free

Details

Home > Chemical Encyclopedia > Chemical Technology > Organic Chemical Technology >
 Preparation of 4-tert-Butylcyclohexanone
  • Preparation of 4-tert-Butylcyclohexanone
  • (CAS NO.: ), which is also known as , 4-(1,1-dimethylethyl)-, could be produced through the following synthetic routes.

    Preparation of 4-tert-Butylcyclohexanone

    A 1-l., three-necked, round-bottomed flask equipped with a mechanical stirrer, a thermometer, a dropping funnel, and an argon-inlet tube is charged with 8.0 g. (0.060 mole) of N-chlorosuccinimide and 200 ml. of toluene. While a continuous positive argon pressure is maintained, the solution is stirred and cooled to 0°, and 6.0 ml. (0.10 mole) of methyl sulfide is added. A white precipitate appears immediately after addition of the sulfide. The mixture is cooled to -25° using a carbon tetrachloride-dry ice bath, and a solution of 6.24 g. (0.0400 mole) of 4-tert-butylcyclohexanol (mixture of cis- and trans-) in 40 ml. of toluene is added dropwise over 5 minutes. The stirring is continued for 2 hours at -25°before a solution of 6.0 g. (0.59 mole) of triethylamine in 10 ml. of toluene is added dropwise over 3 minutes. The cooling bath is removed; after 5 minutes 400 ml. of diethyl ether is added. The organic layer is washed with 100 ml. of 1% hydrochloric acid, then with two 100-ml. portions of water, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The residue is transferred to a 50-ml., round-bottomed flask and distilled bulb to bulb at 120° (25 mm.), yielding 5.54–5.72 g. (90–93%) of 4-tert-butylcyclohexanone, m.p. 41–45°.

    Notice: has been identified as a carcinogen; OSHA has issued emergency standards on its use. All procedures involving benzene should be carried out in a well-ventilated hood, and glove protection is required.


    Prev:No record
    Next:No record
  • Back】【Close 】【Print】【Add to favorite
Periodic Table
    Hot Products