Peracetic Acid → HCID 59001677, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 mL, three-necked round bottom flask (fitted with a reflux condenser, addition funnel, and stir bar) was added undecenamide according to the above formula (10) (4.07 g, 10.0 mmol, 20.0 mmol double bonds) and methylene chloride (50 mL). To the addition funnel was added a solution of sodium acetate (0.17 g) in 32 wt % peracetic acid (5.05 mL of 32 wt %, 5.71 g of 32 wt %, 1.83 g peracetic acid, and 24.0 mmol peracetic acid). The peracetic acid solution was added dropwise over 20 minutes to the suspension of formula (10) in methylene chloride, which had been cooled to 15° C. The reaction mixture was stirred at 25° C. for one hour, during which time the amide dissolved/reacted. The reaction mixture was then heated at reflux for 15 hours. The reaction mixture was then cooled to 15° C. in an ice bath, after which a solution of sodium sulfite (3.02 g, 24.0 mmol) in water (30 mL) was added dropwise to the reaction mixture. The organic and aqueous layers were then separated. The organic solution was washed consecutively with equal volumes of water, 5% (w/v) NaCl (twice), and 5% (w/v) NaHCO3 (twice). The organic layer was then dried over MgSO4, filtered, and solvent was removed under reduced pressure to yield a white solid. The crude product was recrystallized from acetone (100 mL) to which water (1 mL) had been added. The recrystallized product was dried in vacuo at 25° C. for 4 hours. The thus obtained polyepoxy amide is represented by formula (11) shown below. Yield: 1.65 g (38%). M.P. 119-122° C. Epoxide equivalent weight (EEW): 224.6 g/mol epoxide (calculated EEW=219.3).

Provenance & Evidence