Sodium Hydroxide → 5,6-Bis(nitrooxy)hexan-1-ol

To a solution of 5,6-bis(nitrooxy)hexyl acetate (31.3 g, 118 mmol) in THF-EtOH (1:1, 0.492 M) at 0° C., was added a solution of sodium hydroxide (2 N, 126 mL, 251 mmol, 2.1 equiv) dropwise over 5 min. The reaction was stirred at rt for 2 h. The reaction mixture was quenched with a saturated NaHCO3 solution and extracted 3 times with EA. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The product was purified by combi-flash 2×120 g silica gel cartridge using gradient (0-5% in 5 min, 5-55% in 30 min, 55-70% BA/Hex in 10 min) to afford the desired product (24.5 g, Yield=92%) as a pale yellowish oil. 1H NMR (500 MHz, acetone-d6): δ 5.53-5.47 (m, 1H), 5.00 (dd, 1H), 4.72 (dd, 1H), 3.55 (d, 2H), 3.50 (t, 1H), 1.88-1.80 (m, 2H), 1.58-1.51 (m, 4H).

1. customThe reaction mixture was quenched with a saturated NaHCO3 solution
2. extractionextracted 3 times with EA
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customevaporated
7. customThe product was purified by combi-flash 2×120 g silica gel cartridge
8. custom(0-5% in 5 min, 5-55% in 30 min, 55-70% BA/Hex in 10 min)

ORD record

ord-f59daa303ae5412e9353ed3072451837

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622502B2