2,3,4,5-tetrahydro-1-benzoxepin-5-ol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 121.9 g (0.752 mole) of 2,3-dihydro-1-benzoxepin-5(4H)-one are dissolved in 1,400 ml of methanol and, while stirring vigorously, 18.5 g (0.489 mole) of sodium borohydride are introduced in portions so that the temperature remains below 20° C. The mixture is subsequently stirred for 2 hours, most of the solvent is distilled off in vacuo, and the residue is taken up in ethyl acetate. The organic phase is washed with water, 1N potassium bisulfate solution, water and saturated sodium chloride solution and dried over sodium sulfate. The mixture is filtered, and the solvent is evaporated off in vacuo. The oil crystallizes after some time. remains below 20° C The mixture is subsequently stirred for 2 hours, most of the solvent is distilled off in vacuo The organic phase is washed with water, 1N potassium bisulfate solution, water and saturated sodium chloride solution dried over sodium sulfate The mixture is filtered the solvent is evaporated off in vacuo The oil crystallizes after some time

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 800 ml of toluene are poured over 53 g (0.323 mole) of 5-hydroxy-2,3,4,5-tetrahydro-1-benzoxepin and, with addition of 3.7 g of p-toluenesulfonic acid monohydrate, the mixture is refluxed with a water trap for 1.5 hours. The cold organic phase is washed with saturated sodium bicarbonate solution, water and sodium chloride solution, and the solvent is evaporated off in vacuo. Kugelrohr distillation at 30°-35° C./0.008 torr results in 44 g of oil. p 1H NMR (60 MHz/CDCl3): δ=7.23-6.70 (m, 4H); δ=6.30 (m, 1H); δ=6.07-5.70 (m, 1H); δ=4.20 (t, J=5 Hz, 2H); δ=2.63 (m, 2H). the mixture is refluxed with a water trap for 1.5 hours The cold organic phase is washed with saturated sodium bicarbonate solution, water and sodium chloride solution the solvent is evaporated off in vacuo Kugelrohr distillation at 30°-35° C./0.008 torr