4,6-Di-t-butyl-2-cinnamylphenol → 2,4-Di-tert-butyl-6-(3-phenylpropyl)phenol

Participants

Reaction Steps

4,6-Di-t-butyl-2-cinnamylphenol (11.0 g., prepared as described in Example 1) was hydrogenated at room temperature and pressure in tetrahydrofuran (100 ml.) in the presence of 5% palladium on charcoal. The reaction was allowed to proceed until uptake of hydrogen ceased. The mixture was filtered and the filtrate evaporated to an oil. Distillation of the oil gave the desired compound as a colorless oil, b.p. 186°-187°C. at 0.5 mm. Hg. The nmr spectrum at 100 MHz in CDCl3 exhibited absorbances as follows: a singlet (9 protons) at δ 1.30, a singlet (9 protons) at δ 1.43, a multiplet (2 protons) at δ 1.85-204, a multiplet (4 protons) at δ 2.50-2.80, a singlet (1 proton) at δ 4.58, a doublet (1 proton) at δ 6.99 (J = coupling constant = 2.0 Hz), and a multiplet (6 protons) at δ 7.13-7.36.

Provenance & Evidence