3-Phenylprop-2-En-1-Ol → HCID 320666, compound

Participants

Reaction Steps

A mixture of 1,2-dihydroxy-5-methylbenzene (124 g.) and cinnamyl alcohol (134 g.) in 2% aqueous citric acid (1.5 l.) containing ascorbic acid (10.0 g.) was boiled at reflux for 20 hours. After cooling, an oily layer separated and was collected and distilled to give 4-cinnamyl-5-methyl-1,2-dihydroxybenzene (119 g.) as a colorless oil, b.p. 205°-230° at 1.0 mm Hg. The oil was crystallized from a benzene/low-boiling petroleum ether (1/1) mixture to give colorless needles, m.p. 85°. Found: C, 79.9; H, 6.68. Calculated for C16H16O2 : C, 80.0; H, 6.71. The 100 MHz nuclear magnetic resonance (nmr) spectrum of this compound in deuterated chloroform exhibited a singlet (3 protons) at δ 2.07, a doublet (2 protons) at δ 3.37 (J = coupling constant = 5.0 Hz), a singlet (2 protons) at δ 5.02, a multiplet (2 protons) at δ 6.23-6.31, a singlet (1 proton) at δ 6.65, a singlet (1 proton) at δ 6.68, and a multiplet (5 protons) at δ 7.10-7.38.

Provenance & Evidence