Potassium Bromide → 3-(3-Methylcyclohexyl)propanal

Temperature

35 °C

In a 2 L three-necked round-bottom flask equipped with a mechanical stirrer and a reflux condenser were introduced a solution of 3-(3-methylcyclohexyl)propan-1-ol (23.3 g, 0.15 mol) in dichloromethane (140 mL), a solution of potassium bromide (1.77 g, 15 mmol, 0.1 eq) in water (25 mL) and 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO, 300 mg, 1.92 mmol, 0.01 eq). To this mixture was added 0.35M aqueous sodium hypochlorite (594 mL). The mixture was stirred for 3 days at 35° C. then extracted with dichloromethane (500 mL). The organic layer was washed with water (300 mL), 1N HCl (300 mL) and brine (300 mL), dried over sodium sulphate and concentrated. The crude product was chromatographed on silica gel with 8% EtOAc in hexane as elution agent, followed by a bulb-to-bulb distillation (0.01 mBar, 79° C.) to give pure 3-(3-methylcyclohexyl)propanal (11.8 g, gc purity>98%; yield=51%).

1. customIn a 2 L three-necked round-bottom flask equipped with a mechanical stirrer and a reflux condenser
2. extractionthen extracted with dichloromethane (500 mL)
3. washThe organic layer was washed with water (300 mL), 1N HCl (300 mL) and brine (300 mL)
4. dry with materialdried over sodium sulphate
5. concentrationconcentrated
6. customThe crude product was chromatographed on silica gel with 8% EtOAc in hexane as elution agent
7. distillationfollowed by a bulb-to-bulb distillation (0.01 mBar, 79° C.)

ORD record

ord-9515c015398b41109638afd7bf5d584d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08709994B2