Reductive and oxidative synthesis of saturated and unsaturated fatty aldehydes.
Saturated and unsaturated fatty aldehydes were synthesized 99+% pure with yields of up to 80% by the reduction of 1-acylaziridines with lithium aluminium hydride, and in yields of up to 87% by oxidation of the corresponding alcohol with 1-chlorobenzotriazole. It was found for the reduction that optimum aldehyde yield was obtained with a mole ratio of reactants, consisting of acid chloride-ethylenimine-triethylamine-LiAlH(4), equal to 1:2:2:2. Optimum conditions for alcohol oxidation were found to be a mole ratio of oxidant to alcohol of 1:1.3 with refluxing for 45 min in methylene chloride containing 25% pyridine. Methods for the purification of the final product are also described. Purity criteria were thin-layer and gas-liquid chromatography and infrared and nuclear magnetic resonance spectroscopy.
D000447:Aldehydes / Q000138:chemical synthesis*; D000535:Aluminum; D001389:Azirines; D055598:Chemical Phenomena; D002621:Chemistry; D002713:Chlorine; D002855:Chromatography, Thin Layer; D005021:Ethylamines; D005230:Fatty Acids, Nonesterified; D005233:Fatty Alcohols; D007097:Imines; D007259:Infrared Rays; D008041:Linoleic Acids; D008094:Lithium; D009682:Magnetic Resonance Spectroscopy; D009829:Oleic Acids; D010084:Oxidation-Reduction; D010169:Palmitic Acids; D013053:Spectrophotometry; D014230:Triazoles
D000447:Aldehydes; D001389:Azirines; D005021:Ethylamines; D005230:Fatty Acids, Nonesterified; D005233:Fatty Alcohols; D007097:Imines; D008041:Linoleic Acids; D009829:Oleic Acids; D010169:Palmitic Acids; D014230:Triazoles; D002713:Chlorine; D008094:Lithium; D000535:Aluminum