Reaction #802692

Reaction equation

sodium bromate

Isopropanol

Methyl 3-hydroxycyclohexanecarboxylate

→

methyl 3-oxocyclohexanecarboxylate

Yield 100.0%

Solvents

diethyl ether

water

ether

Conditions

Workup

1. 1
   Temperaturecooled in an ice bath
2. 2
   Otherto go above 30° C
3. 3
   workup.STIRRINGThe reaction mixture was stirred for 1 h with the reaction temperature at ˜15° C
4. 4
   Otherat ˜27° C
5. 5
   OtherThe layers were separated
6. 6
   Washthe organic layers were washed with ether
7. 7
   WashThe combined organics were washed with saturated aqueous NaHCO3 solution and brine
8. 8
   DryingThe organics were then dried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Concentrationconcentrated

Procedure

Ruthenium (IV) oxide hydrate (1.47 g, 11.1 mmol) and sodium bromate (100 g, 664 mmol) were combined in diethyl ether (600 mL) and water (300 mL). The resulting black mixture was stirred for 10 min and then cooled in an ice bath. Methyl 3-hydroxycyclohexanecarboxylate (35 g, 221 mmol) was dissolved in ether (to bring total volume to 100 mL) and was added dropwise to the ice cold reaction mixture. The temperature was not allowed to go above 30° C. The reaction mixture was stirred for 1 h with the reaction temperature at ˜15° C. Isopropanol was carefully added to the reaction mixture at a rate necessary to keep the reaction temperature at ˜27° C. The layers were separated and the organic layers were washed with ether. The combined organics were washed with saturated aqueous NaHCO3 solution and brine. The organics were then dried over MgSO4, filtered, and concentrated to provide methyl 3-oxocyclohexanecarboxylate (34.5 g, 100% yield) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 3.68 (s, 3H), 2.79 (m, 1H), 2.52 (d, J=7.78 Hz, 2H), 2.23-2.42 (m, 2H), 1.98-2.15 (m, 2H), 1.82 (d, J=10.29 Hz, 1H), 1.61-1.77 (m, 1H).

Source