Hydrochloric Acid → 3-(Tridec-1-ynyl)benzyl alcohol

Participants

Reaction Steps

To a solution of 3-(Tridec-1-ynyl)benzaldehyde (5.68 g, 20 mmol, from example 5) in THF (70 ml) at -78° C. was added DIBAL (22 ml, 1.1 eq, 1 molar solution in hexane). After warming slowly to room temperature the solution was stirred for 2 hr and then added to dilute hydrochloric acid (50 ml). The product was then extracted into diethyl ether (2×100 ml) and after washing with brine and drying (MgSO4) the ether was removed under reduced pressure. Distillation of the resulting oil yielded the desired product, (4.55 g, 79.5%), B.p. 210° C. at 0.1 mm Hg, νmax 690, 785, 1030, 1460, 1600, 2200, 2850, 2915 and 3300 cm-1 ; δ(CDCl3) 0.92 (3H, distorted t, terminal CH3), 1.3 (18H, m, alkylene chain), 1.9 (1H, s, hydroxyl), 2.35 (2H, t J= 7 Hz, CH2 adjacent to acetylene), 4.6 (2H, s, benzylics), 7.3 (4H, m, aromatics). M+ 286.2301, (C20H30O requires 286.2297).

Provenance & Evidence