2-Ethylhexanol → HCID 19003306, compound

Participants

Reaction Steps

Into a 125 ml reaction flask equipped with a magnetic stirrer, thermometer, condenser and nitrogen atmosphere were placed 5.0 g (0.013 mol) of the acid chloride of Example 2, 1.7 g (0.013 mol) 2-ethylhexanol and 50 ml of 2% dimethylformamide in methylene chloride. This mixture was stirred during the addition of 2.8 g (0.028 mol) triethylamine in 5 ml methylene chloride. This addition produced an exotherm of about 10° C. The reaction was then refluxed for 1 hour. The mixture was cooled and transferred to a separatory funnel with 100 ml methylene chloride and 250 ml water. The ensuing emulsion was filtered, put back in the funnel and the phases separated. The organic phase was extracted with 50 ml water and 50 ml 5% sodium bicarbonate. The organic solution was dried with anhydrous magnesium sulfate and the solvent stripped using aspirator and high vacuum. Liquid chromatographic analysis of the white solid product indicated the presence of two components. The material was redissolved in methylene chloride and extracted with two 50 ml portions of 5% sodium hydroxide. The organic solution was again dried and stripped and the residue recrystallized from 80/20 ethanol/water. After isolation and drying, 1.5 g of slightly yellow product were obtained (melting 129°-131° C.). The infrared spectrum (KBr pellet) showed the carbonyl absorption at 1720 cm-1 (imide and ester). The NMR spectrum showed the anticipated aromatic ring (7.7-7.9 ppm, doublet, 1H; 8.2-8.5, multiplet, 2H) and the 2-ethylhexyl and HALS groups [4.4-4.9 ppm, multiplet, 1H; 4.2-4.3 ppm, doublet, 1H; 0.7-2.3 ppm, several multiplets including two singlets (1.2 and 1.3 ppm)].

Provenance & Evidence