Sodium Hydroxide → 4,5-Bis(nitrooxy)pentyl alcohol

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Reaction Steps

To a solution of 18.7 g of 4,5-bis(nitrooxy)pentyl acetate in 150 mL of EtOH at 25° C. was added 2.96 g of NaOH. The mixture was stirred for 90 min, quenched by addition of NaHCO3 sat., extracted with EtOAc, washed with brine and dried over sodium sulfate. Purification by flash chromatography afforded 6.3 g of the desired compound as an orange oil. 1H NMR (acetone-d6, 500 MHz): δ 5.56 (m, 1H), 5.01 (dd, 1H), 4.73 (dd, 1H), 3.68 (t, 1H), 3.60 (m, 2H), 1.93-1.86 (m, 2H), 1.69-1.64 (m, 2H).

Provenance & Evidence