ChemicalBook CAS DataBase List 4-tert-Butylcyclohexanone

4-tert-Butylcyclohexanone synthesis

9synthesis methods

Product Name:4-tert-Butylcyclohexanone
CAS Number:98-53-3
Molecular formula:C10H18O
Molecular Weight:154.25

N-Chlorosuccinimide (NCS) (8.0 g, 0.060 mol) and toluene (200 mL) were cooled to 0 C° in a 1-L, threenecked, round-bottomed flask equipped with a mechanical stirrer, a thermometer, a dropping funnel, and an argon inlet tube. Dimethyl sulfoxide (6.0 mL, 0.10 mol) was added and the mixture was cooled to -25 C° using a tetrachloromethane/dryice bath. A solution of 4-tert-butylcyclohexanol (6.24 g, 0.04 mol; mixture of E and Z isomers) in toluene (40 mL) was added dropwise over 5 min, stirring was continued for 2 h at -25 C°, and then a solution of triethylamine (6.0 g, 0.06 mol) in toluene (10 mL) was added dropwise over 3 min. The cooling bath was removed, and, after 5 min, diethyl ether (400 mL) was added. The organic phase was washed with 1% aq. hydrochloric acid (100 mL) and then with water (2 × 100 mL), and dried over anhydrous magnesium sulfate. The solvents were evaporated under reduced pressure, and the residue was transferred to a 50-mL, round-bottomed flask and bulb-to-bulb distilled at 120 C° (25 mmHg) to yield 5.72 g (93%) of 4-tertbutylcyclohexanone 1794; mp 41–45 C°. Recrystallization from petroleum ether at -20 C° gave an 88% recovery of 1794 with mp 45–46 C°.

98-52-2 Synthesis

98-52-2
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98-53-3
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Yield:98-53-3 100%

Reaction Conditions:

with pyridine;trichloroisocyanuric acid in ethyl acetate at 20; for 0.333333 h;Reagent/catalyst;

Steps:

Oxidation of 4-t-butylcyclohexanaol
General procedure: O.1 mole of 4-t-butylcyclohexanol (ACROS) was weighed and placed in a 50 mL Erlenmeyer flask with stir bar and 10 mL ethyl acetate (Fisher). 1.0 g trichloroisocyanuric acid (Leslie’s Swimming Pool Supplies) was weighed into a 30 mL beaker and dissolved in 10 mL ethyl acetate. 1.0 mL (0.12 mol) pyridine (Aldrich) was delivered to the alcohol mixture by pipet. The TCICA solution was transferred to a dropping funnel and added dropwise to the stirring alcohol solution. Following addition, stirring was continued for 20 minutes and the mixture was filtered. The filtrate was washed with 10 mL 1 M HCl, 10 mL 5% NaHCO₃, and 5 mL saturated NaCl. The organic layer was dried over MgSO₄, a GC sample removed, filtered and evaporated to dryness. Yield 1.50 g (100%), nmr attached.

References:

Dip, Irene;Gethers, Christina;Rice, Tonya;Straub, Thomas S. [Tetrahedron Letters,2017,vol. 58,# 28,p. 2720 - 2722] Location in patent:supporting information

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