Sodium Hydroxide → Glyceryl 1,2-Dinitrate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.5 g of 2,3-bis(nitrooxy)propyl acetate in 25 mL of ethanol at 0. ° C. was added 469 mg of crushed NaOH powder. The reaction was stirred at 0° C. for 15 min upon which a cloudy suspension had formed. The resulting mixture was then poured onto ice cold 5% HCl and then extracted 3× with ether. The organics were combined and evaporated to remove most of the ethanol. The oil was then redissolved in ether, dried (Na2SO4), filtered and concentrated in vacuo to give a pale yellow oil which was used immediately without further purification. 1H NMR (500 MHz, acetone-d6): δ 5.59-5.52 (m, 1H), 5.05 (dd, 1H), 4.86 (dd, 1H), 4.60-4.50 (bs, OH), 3.95 (dd, 2H).

Provenance & Evidence