Hydrochloric Acid → 1-(3-Hydroxyphenyl)-oct-1-yne

Participants

Reaction Steps

1-(3-Methoxyphenyl)-oct-1-yne, (6.50 g, 0.03M), was dissolved in 2,4,6-collidine, (100 ml), and anhydrous lithium iodide (20.08 g, 0.15M), added. The reaction was stirred under nitrogen at reflux temperature for 48 h, then cooled and poured intro water, (500 ml), and acidified with dilute hydrochloric acid. The product was extracted into ethyl acetate, (twice), and the organic phases combined, washed with water (twice) and dried, (MgSO4). Evaporation of the solvent in vacuo yielded the crude product as a brown oil, which was purified by chromatography on silica gel, eluting with dichloromethane/n-hexane [1:1] to chloroform. 5.40 g (90%) of product was collected as a colourless oil. νmax (film) 1580, 1590, 1605, 2230 (weak) 3400 cm-1 ; δ(CDCl3) 0.85 (3H, distorted t, terminal CH3), 1.39 (8H, m, alkylene chain), 2.32 (2H, t, J 6 Hz, acetylenic CH2), 4.77 (1H, s, OH, exchanged with D2O), 6.78 (2H, m, aromatics), 7.02 (2H, m, aromatics).

Provenance & Evidence