2-Chloroethanol → 2-Chloroethyl perfluorooctanoate

Participants

Reaction Conditions

Reaction Steps

2-Chloroethyl perfluorooctanoate was prepared by adding 162 g (0.375 mol) of perfluorooctanoyl chloride to 32.2 g (0.40 mol) of 2-chloroethanol cooled at 0° C., stirring the resulting mixture at 0° for 2 h, and then stirring for about 2.5 days at 25°. Fractionation of the resulting solution gave 152.6 g (85% yield) of the chloroethyl ester, b.p. 84°-88° at 1.3 kpa (10 mm), 98% pure by GC. IR (CCl4): 2960 (sat'd CH), 1790 (C--O), 1300-1100 cm31 1 (CF, C-O). NMR (CCl4): 1H 4.59 (t, JHH 5.5 Hz, 2H, CH2) and 3.70 ppm (t, JHH 5.5 Hz, 2H, CH2); 19F -81.6 (t of t, JFF 10, 4 Hz, 3F, CF4), -119.0 (t of t, JFF 12, 6 Hz, 2, F, CF2C=O), -122.4 (m, 4F, CF2), -123.3 (m, 4F, CF2), and -126.8 ppm (m, 2F, CF2).

Provenance & Evidence