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

Participants

Reaction Steps

2,6-Di-t-butyl-4-cinnamylphenol (30 g., prepared as described in Example 2) was catalytically 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 was evaporated to an oil. Distillation of the oil gave the desired compound (25 g.) as an oil, b.p. 195°-200°C. at 10.5 mm. Hg. The nmr spectrum in CDCl3 at 100 MHz exhibited absorbances as follows: a singlet (9 protons) at δ 1.40, a singlet (9 protons) at δ 1.43, a multiplet (2 protons) at δ 1.75-2.10, a multiplet (4 protons) at δ 2.43-2.82, a singlet (1 proton) at δ 5.00, a singlet (2 protons) at δ 6.98, and a multiplet (5 protons) at δ 7.08-7.40.

Provenance & Evidence