The antioxidant methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate

Acta Crystallogr C Struct Chem. 2014 Nov;70(Pt 11):1050-3. doi: 10.1107/S2053229614021445. Epub 2014 Oct 15.

Abstract

The title compound, C18H28O3, was prepared by the reaction of 2,6-di-tert-butylphenol with methyl acrylate under basic conditions using dimethyl sulfoxide as the promoter. The structure of this antioxidant indicates significant strain between the ortho tert-butyl substituents and the phenolic OH group. In spite of the steric crowding of the OH group, it participates in intermolecular hydrogen bonding with the ester carbonyl O atom.

Keywords: antioxidant; crystal structure; hindered phenol; hydrogen bonding.