Triethyl phosphite → Octanoic acid, 2-(diethoxyphosphinyl)-, ethyl ester

Participants

Reaction Steps

2-Bromo octanoic acid ethyl ester (50 g, 0.2M) was heated at 150° with triethyl phosphite (75 g, 0.44M) and the distillate, Bpt 37°-60° condensed as the temperature was raised to 200° over 6 h. The reaction mixture was cooled and distilled under high vacuum (1.00 mm Hg) to afford 2 main fractions (a) Triethyl phosphite b.p. 40°-70° and (b) 2-(diethylphosphono)octanoic acid ethyl ester (49.5 g, 0.16M); b.p. 120°-130° at 0.5 mm Hg. (Found: C, 52.9; H, 9.4. C14H29O5P+0.5H2O requires: C, 53.0; H, 9.5%; δ(CDCl3) 0.88 (3H, m, CH3); 1.32 (17H, m, (CH2)4, 3×CH3); 1.9 (2H, m, CH2); 2.92 (1H, d, d, d, J= 22 Hz, J=10 Hz; J=4 Hz, CH--P); 4.18 (6H, m, 3×CH2O).

Provenance & Evidence