1-Octanol → Octanal

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 1.0 g (3.56 equivalents of sulfide group) of poly (p-methylmercaptostyrene) in dichloromethane (20 ml) was added at -10°C a solution of 280 mg (3.94 mmoles) of chlorine (as cl2) in 10 ml of CH2Cl2, after which the mixture was cooled to -78°C, treated with 130 mg (1 mmole) of octanol in 1.6 ml of CH2Cl2, and stirred at -78°C for 0.5 hr., and then -25°C for 4.5 hours. The reaction mixture was treated at -25°C with 612 mg (6 mmoles) of triethylamine in 2 ml of CH2Cl2 and stirred for an additional 20 minutes. Ether (50 ml) was next added, and after stirring for 10 minutes, the resulting mixture was filtered and the beads washed with another 30 ml of ether. The combined filtrate was next washed with 1 N HCl solution and brine, and dried (MgSO4). After removal of the solvent by evaporation under reduced pressure, the product was evaporatively distilled (bulb to bulb) at an oven temperature of 50°C and 0.1 mm pressure to yield 122 mg (95%) of octanal. GLC analysis (4% SE-30) of the product indicated the presence of 97% octanal and 3% starting material.

Provenance & Evidence