Ammonia → 1-(2-Hydroxyphenyl)-oct-1-yne

Beteiligte Stoffe

Reaktionsschritte

To a grey suspension of lithium amide [lithium shot, (0.59 g, 0.085M) in liquid ammonia (250 ml)] at -30° C. was added 2-hydroxyphenyl acetylene (50 g, 0.042M, prepared by the method of G. A. Russell et al, J. Org. Chem. 31, 248 (1966)) in dry tetrahydrofuran (50 ml). The solution was stirred at reflux for 1 h, then iodohexane (8.91 g, 0.042M), in dry tetrahydrofuran (50 ml) was added dropwise. The reaction was refluxed for 6 h, then the ammonia allowed to evaporate overnight. The resultant pale brown solution was refluxed for 18 h, then cooled and poured into water. Acidified with dilute sulphuric acid and extracted into diethyl ether (twice). The combined organic phases were washed with water (twice), saturated brine and dried (MgSO4). Evaporation in vacuo yielded a red oil which was purified by distillation to give 6.80 g (80%) of the product as a colourless oil. νmax (film) 1463, 1485, 1575, 1608 (weak), 2225 (weak), 3500 cm-1, δ(CDCl3) 0.89 (3H, distorted t, terminal CH3) 1.40 (8 H, m, alkylene chain), 2.43 (2H, t, J 7 Hz, acetylenic CH2), 5.80 (1H, s, OH), 6.87 (2H, m, aromatics) 7.22 (2H, m, aromatics).

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