Stearyl Alcohol → Octadecyl DI-tert-butyl-4-hydroxyhydrocinnamate

Participants

Reaction Conditions

Reaction Steps

109 g (0.374 mol) of β-(3,5-di-tert-butyl4-hydroxyphenyl)propionic acid methyl ester, 92.5 g (0.34 mol) of stearyl alcohol and 0.1 g of lithium acetate in the dihydrate form (0.001 mol) are introduced into a vessel and melted and stirred at 100° C. under nitrogen. As soon as a melt is obtained, cautiously evacuation is carried out and at the same time the melt is heated to an internal temperature (IT) of from 150 to 160° C. The methanol formed is distilled off and condensed in a cold trap. As soon as an internal pressure of <10 mbar is reached, the internal temperature (IT) is increased to from 170 to 180° C. and further evacuation to <1 mbar is carried out. As soon as IT=180° C. and a pressure of <1 mbar is reached, those conditions are maintained for one hour and then, in the course of from 1 to 2 hours at IT=200-210° C., the excess β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid methyl ester is removed by distillation. The reaction melt then contains <0.2% starting materials and has a content of >98% β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid octadecyl ester. The reaction melt is cooled, and left to stand for crystallisation. Yield 96.5%; m.p. 51° C.

Provenance & Evidence