Stearic Acid → 3-Stearamidopropyl 3(3,5-di-tert-butyl-4-hydroxyphenyl)propionate

Participants

Reaction Steps

Stearic acid (56.8 g; 0.2 mole) was added to a hot (80° C.) mixture of 30 g (0.4 mole) 3-aminopropanol, 100 ml xylene and 0.5 g sodium methoxide. The mixture was heated at reflux for two hours with removal of water and was then poured into hexane, in which N-(3-hydroxypropyl)stearamide crystallized and was obtained by filtration; it melted at 83°-89° C. After the product was recrystallized from acetone, melting point rose to 94°-96° C. A 34.1 g (0.1 mole) portion of this intermediate was heated with 27.8 g (0.1 mole) of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid, 1 g of Tyzor TBT catalyst and 100 ml xylene. After the mixture was refluxed for 3 hours, 2 ml of water was collected in the Stark and Dean trap. The xylene was distilled off under vacuum, and the residue was crystallized from acetonitrile. The title product (29 g) thus obtained melted at 50°-52° C.

Provenance & Evidence