Sodium Hydroxide → 4-Azido-4,4-Dinitro-1-Butyl Acetate

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Reaction Steps

A divided electrochemical H-cell was charged with 4,4-dinitrobutyl acetate (10.2 g), 30% aqueous NaN3 (25 mL) and 12N NaOH (4 mL) in the anode compartment and 30% NaN3 (35 mL) in the cathode compartment. This solution was electrolyzed at 650 mA using a platimum foil anode (6.5 cm2) and a stainless steel cathode. After 5.25 h the reaction was stopped, and the anolyte was extracted with CH2Cl2 (3×25 mL). Brine-washing, drying, and concentrating the extracts yielded a product which displayed a weak hydroxyl absorption in the infrared spectrum. The product was reacetylated by stirring with acetyl chloride (1 mL) in CH2Cl2 (30 mL) for 2 h. This reaction was quenched in ice water, dried, and concentrated. The crude yellow oil was purified by column chromatography on silica gel eluting with 10% ethyl acetate in hexanes. The purified product was a clear light yellow oil which was greater than 95% pure by HPLC: nD =1.4649 (25° C.); IR: 2165, 1735, and 1590 cm-1 ; NMR (CDCl3): 4.07 (q, 2H), 2.58 (m, 2H), 2.07 (s, 3H), 1.73 (m, 2H). Elemental analyses calculated for C6H9N5O6 : C, 29.15; H, 3.64; N, 28.34. Found: C, 29.59; H, 3.90; N, 27.89.

Provenance & Evidence