3-Phenylprop-2-En-1-Ol → 2,6-Di-tert-butyl-4-(3-phenylprop-2-en-1-yl)phenol

Participants

Reaction Steps

Cinnamyl alcohol (134 g.) was added to a suspension of 2,6-di-t-butylphenol (206 g.) in 88% aqueous formic acid (470 ml.) and glacial acetic acid (200 ml.), and the mixture was refluxed for 1.5 hours. Warm water (2000 ml.) was added and the oily layer which formed on top of the mixture was collected. The oil was distilled and gave a fraction (179 g.), b.p. 190°-200° C. at 0.5 mm Hg. The oil crystallized upon treatment with Skelly F (a mixture of petroleum hydrocarbons boiling between 30°-60° C.) to give glistening, colorless needles, m.p. 93° C. (Found: C, 85.7; H, 9.20. Calc. for C23H30O: C, 85.7; H, 9.38). The nuclear magnetic resonance (nmr) spectrum of this compound at 100 MHz in deuterated chloroform (CDCl3) exhibited absorbances as follows: a singlet (9 protons) at δ 1.41; a singlet (9 protons) at δ 1.45; a singlet (2 protons) at δ 3.48; a singlet (1 proton) at δ 5.07; a multiplet (2 protons) at δ 6.18-6.58; and a multiplet (7 protons) at δ 6.96-7.46.

Provenance & Evidence