Triethylamine → HCID 23369169, compound

Participants

Reaction Steps

1.87 g (0.018 mol) of methacrylyl chloride and a small amount of di-t-butylhydroxytoluene in methylene chloride are added to a solution of 8 g (0.0148 mol) of 11,14,17,20,23,26,29,32,35-Nonaoxahexatriacontan-1-ol and 1.82 g (0.018 mol) of triethylamine in 40 ml of methylene chloride at a temperature of -20° C. The mixture is stirred at room temperature for 12 hours, without cooling. The solvent is removed at room temperature and the crude product is worked up by flash chromatography over silica gel 60 (0.040-0.063 mm) using acetone/ether 50:50. The mobile phase is distilled off at room temperature and the product is obtained as a colorless liquid. 1HNMR: 1.2-1.8 ppm (m, 16H, (--CH2)8 --), 1.9 ppm (s, 1H, HO--), 3.4 ppm (s, 3H, --OCH3), 3.7 ppm (m, 34H, --(OCH2CH2)8 --O--),--(CH2)8 --CH2 --O--), 4.2 ppm (m, 2H, --COO--CH2 --CH 2 --), 5.5 ppm (s, 1H, H--CH=C(CH3)--COO--), 6.1 ppm (s, 1H, H--CH=C(CH3)--COO--). IR (film): 1700 cm-1 (C=O), 1620 cm-1 (C=C), 1110 cm-l (C--O).

Provenance & Evidence