Benzene → 5-Methyl-5-nitro-1,3-dioxane

Participants

Reaction Steps

2-Nitro-2-methyl-1,3-propanediol 405.00 grams (3.00 moles), 98% trioxane 92.80 grams (1.00 mole), p-toluenesulfonic acid 3.00 grams (0.016 mole), and benzene 600 ml were placed in a two liter three-necked RB flask. The flask was fitted with a thermometer, a mechanical stirrer and a Dean-Stark trap connected to a condenser. The mixture was stirred and refluxed. The slurry gradually became a homogeneous solution (usually about 30 minutes after heating started) and the benzene-water azeotrope started to distill over. Refluxing was continued until 45 ml of water was collected (i.e., approximately four hours). During this period the solution temperature was between 78° C. and 82° C. After 45 ml of water had been collected, the reaction mixture was cooled and neutralized with 3 ml triethylamine. Benzene was distilled from the clear solution first at atmospheric pressure (approximately 415 ml benzene was recovered at a solution temperature of 82° C.-100° C.) and then at about 125 mm of pressure (approximately 120 ml benzene was recovered at a solution temperature of about 48° C.-110° C.). A clear, pale-yellow, viscous liquid, 450.67 grams, containing a mixture of the reaction products polynitroformal and 5-methyl-5-nitro-1,3-dioxane was obtained as the resulting product.

Provenance & Evidence