Sodium Hydroxide → Glyceryl 1,2-Dinitrate

Temperature

0 °C

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).

1. customhad formed
2. additionThe resulting mixture was then poured onto ice cold 5% HCl
3. extractionextracted 3× with ether
4. customevaporated
5. customto remove most of the ethanol
6. dissolutionThe oil was then redissolved in ether
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a pale yellow oil which
11. customwas used immediately without further purification

ORD record

ord-bc5a1a43b9e141f6aee726600c0c4b6c

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622501B2