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

Participants

Reaction Steps

To a tetrahydrofuran/ethanol 1:1 (12 mL) solution of 5,6-bis(nitrooxy)hexyl 4-nitrobenzoate (2.5 g, 6.70 mmol) at 0° C. was added 2.5 N sodium hydroxide (6.5 mL) dropwise. The solution was stirred at room temperature for 3 hours. The solution was diluted with a solution of sodium bicarbonate (10 mL) and extracted with ethyl acetate (3×25 mL). The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo, affording the title compound. 1H NMR (300 MHz, CDCl3) δ: 5.45-5.38 (m, 1H), 4.94 (dd, 1H), 4.73-4.67 (m, 1H), 4.43 (t, 1H), 3.40-3.36 (m, 2H), 1.75-1.68 (m, 2H), 1.43-1.36 (m, 4H).

Provenance & Evidence