Water → Cyclohexylbenzene

To a 25-mL three-neck flask were added Rh(acac)(cod) (6.8 mg, 21.8 μmol) and PhB(OH)2 (445 mg, 3.65 mmol), and the atmosphere in the system was substituted with argon. The mixture was added with 3.6 mL of a solution of each ligand (21.8 μmol) in anhydrous dioxane and 2-cyclohexenone (0.073 mL, 0.73 mmol). The mixture was stirred at room temperature for 15 minutes, and added with water (0.18 mL). The reaction mixture was stirred at 100° C. for 3 hours, then added with 9 mL of water, and extracted twice with 9 mL of diethyl ether. The organic layers were combined, washed with 9 mL of saturated sodium chloride solution, and concentrated in an evaporator. The residue was treated by silica gel column chromatography (toluene:ethyl acetate=2:1) to obtain 3-phenylcyclohexane as colorless oil. The resulting optically active 3-phenylcyclohexanone in an amount of 2 mg was dissolved in 1 mL of a mixture of n-heptane and 2-propanol (99:2). This solution was analyzed by HPLC under the following conditions.

1. stirringThe reaction mixture was stirred at 100° C. for 3 hours
2. extractionextracted twice with 9 mL of diethyl ether
3. washwashed with 9 mL of saturated sodium chloride solution
4. concentrationconcentrated in an evaporator
5. additionThe residue was treated by silica gel column chromatography (toluene:ethyl acetate=2:1)

ORD record

ord-b56e743ac49b4ec9a491057b5dc9ad41

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07569730B2