Acetic Acid → 5-(3',5'-Di-tert-butyl-4'-hydroxyphenylethyl)-5-methyl-1-n-octadecylhydantoin

Participants

Reaction Steps

7.8 g (0.12 mole) of potassium cyanide in 40 ml of water is slowly added to a stirred solution of 27.6 g (0.1 mole) of 3,5-di-tert-butyl-4-hydroxyphenylethyl methyl ketone and 27.0 g (0.1 mole) of n-octadecylamine in 200 ml of glacial acetic acid at 15°-25°C. The mixture is stirred at 20°-25°C for 3.5 hours after addition is complete and then allowed to stand overnight at room temperature. The reaction mixture is then diluted with water and extracted with ether. The ether extract is dried and evaporated to dryness. The crude aminonitrile thus obtained is dissolved in 200 ml of glacial acetic acid containing 10 ml of concentrated hydrochloric acid and reacted with 16.2 g (0.2 mole) of potassium cyanate in 50 ml of water. The reaction mixture is warmed at 35°-50°C for 3 hours, then cooled and poured into water. The solid obtained is removed by filtration and then refluxed with 300 ml of 20% aqueous hydrochloric acid for 30 minutes. The solution is cooled and the desired product, 5-(3',5' -di-tert-butyl-4'-hydroxyphenylethyl)-5-methyl-1-n-octadecylhydantoin, is isolated by filtration, washed, dried and recrystallized.

Provenance & Evidence