Potassium Hydroxide → 6-[(7-Ethyl-3-methylnona-2,6-dien-1-yl)oxy]-2,3-dihydro-1-benzofuran

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Reaction Conditions

Reaction Steps

10.9 g. of 6-hydroxy-2,3-dihydrobenzofuran are dissolved in 80 ml. of anhydrous dimethylformamide and treated, while stirring and with ice cooling at 0° C. with 5.3 g. of freshly powdered potassium hydroxide. The mixture is stirred for 1 hour at 0° C. under a nitrogen atmosphere and then added dropwise within 1 hour to a solution of 19.6 g. of 1-bromo-7-ethyl-3-methyl-2,6-nonadiene in 10 ml. of absolute tetrahydrofuran. The mixture is allowed to stir for 2 hours at 0° C. and for 2 hours at room temperature and then poured onto a mixture of 100 ml. of 10% by weight aqueous sodium hydroxide and 100 ml. of ice-water. The mixture is extracted three times with pentane, the extracts are washed successively with 10% by weight aqueous sodium hydroxide, water and saturated sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/diethyl ether (19:1 parts by volume) there is obtained pure 6-[(7-ethyl-3-methyl-2,6-nonadienyl)-oxy]-2,3-dihydrobenzofuran which is distilled in a bulb-tube at 132° C./0.02 mmHg; nD20 = 1.5350.

Provenance & Evidence