Ammonia → 2,4-Octanedione

Participants

Reaction Steps

Metallic sodium (0.3 g, 13 mmol) was added to a liquid ammonia solution (400 ml). After the mixture was dyed blue, iron nitrate hydrate (0.13 g, 0.3 mmol) was added and then again metallic sodium (12.6 g, 0.55 mol) was added. After completion of the NaNH2 formation, a solution of acetylacetone (30 g, 299 mmol) in ethyl ether (20 ml) was added within 10 minutes at -78° C. After 20 minutes, propyl bromide (28.2 g, 299.6 mmol) was added by instillation within 25 minutes. After further stirring for 50 minutes, ethyl ether (100 ml) was added and the ammonia was evaporated. After about 12 hours, the mixture was extracted with ethyl ether 3 times (50 ml each) and the combined organic phases were washed twice with an NaCl solution (50 ml each) and dried on Na2SO4. After removal of the solvent, 33 g of 2,4-octanedion was obtained. After vacuum distillation (13.5 mbars, 78° C.), 22.59 g of 2,4-octanedion, corresponding to a yield of 52.9 percent, was obtained as a colorless oil.

Provenance & Evidence