Azelaic Acid → Nonanedioic acid, bis[(2,2-dimethyl-1-oxopropoxy)methyl] ester

Participants

Reaction Conditions

Reaction Steps

Caesium carbonate (32.6 g; 0.120 mol) was added to a stirred solution of nonanedioic acid (9.4 g; 50.0 mmol), chloromethyl pivalate (15.1 g; 0.10 mmol), and NaI (0,5 g; 3.3 mmol) in dry N,N-dimethylformamide (50 mL). The mixture was stirred for 2 days at ca. 40° C. (bath temperature) under argon. Excess solvent was evaporated off at ca. 35° C. (bath temperature) and 5 to 1 mm Hg. The residue was dissolved in water (50 mL) and diethyl ether (25 mL). The aqueous portion was extracted with ether (1×15 mL) and the combined ether solutions were washed with saturated NaCl solution (1×10 mL) and dried (Na2SO4). Filtration and evaporation left 12.34 g (59%) after pumping out to 0.2 mm Hg. 1H NMR (200 MHz; CDCl3): δ 1.20 (20H, s), 1.32 (4H, s), 1.63 (4H, m), 2.35 (4H, t, J=7.4 Hz), 5.76 (4H, d, J=2.8 Hz). 13C NMR (50 MHz; CDCl3): δ 24.58, 26.84, 28.80, 29.01, 33.92, 38.73, 79.22, 164.87, 172.29, MS(ES):439.3 [M+Na]+.

Provenance & Evidence