1-Octanol → Octanal

Temperature

-78 °C

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.

1. wait, and then -25°C for 4.5 hours
2. stirringstirred for an additional 20 minutes
3. stirringafter stirring for 10 minutes
4. filtrationthe resulting mixture was filtered
5. washthe beads washed with another 30 ml of ether
6. washThe combined filtrate was next washed with 1 N HCl solution and brine
7. dry with materialdried (MgSO4)
8. customAfter removal of the solvent
9. customby evaporation under reduced pressure
10. distillationthe product was evaporatively distilled (bulb to bulb) at an oven temperature of 50°C and 0.1 mm pressure

ORD record

ord-61f6bbd6b421402594b9ad7cad1d8360

Source dataset

uspto-grants-1976_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03959190