Hydroxylamine → HCID 20320276, compound

Participants

Reaction Conditions

Reaction Steps

To a 5000 cc round bottom flask under nitrogen was charged 618.0 g (3.0 moles) 2,6-di-t-butylphenol. To the molten phenol at about 40° C was added 18.0 g (0.33 mole) fresh sodium methoxide powder. The reaction mixture was heated to 75° C with stirring, then cooled back to 60° C. Then was added 284 g. (300 cc, 3.3 moles) methyl acrylate over a 30 minute period. The reaction exothermed and temperature was held at about 80° C with cooling. After the addition was completed the batch was heated 3 hours at 60° C. The reaction was then cooled to 50° C and 9.0 cc conc. H2SO4 was added with stirring as the temperature rose to 60° C. Unreacted methyl acrylate was removed by distillation at reduced pressure. The product was distilled at 128° -130° C (0.3 mm) and recrystallized from hexane to afford 714 g. white crystals, m.p. 66° C. The ester was converted to the aminoalcohol by heating the ester at 150° C for 3 hours with a 100% excess of N-methylethanolamine, while concurrently removing methanol. Excess amine was removed by vacuum distillation at 150° C. The stripped residue product was a sticky glass at room temperature. The yield was about 95%.

Provenance & Evidence