Sodium Chloride → 6-[(2,3-Dihydro-1-benzofuran-6-yl)oxy]-4-methylhex-4-enal

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Reaction Steps

4.64 g. of 6-[(6,7-epoxy-3,7-dimethyl-2,6-nonadienyl)-oxy]-2,3-dihydrobenzofuran (see Example 3) are dissolved in 14 ml. of tetrahydrofuran, diluted with 7.5 ml. of water and treated with a mixture of 0.1 ml. of 70% by weight perchloric acid in 1 ml. of water. The mixture is stirred at room temperature for 4 hours, 10 ml. of saturated aqueous sodium chloride solution are added thereto and the resulting mixture is extracted three times with diethyl ether methylene chloride (9:1 parts by volume). The extracts are washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated. The thus-obtained crude diol is dissolved in 30 ml. of tetrahydrofuran and treated, with ice cooling and under a nitrogen atmosphere, with a solution of 3.2 g. of sodium metaperiodate in 35 ml. of water following which the mixture is stirred overnight at room temperature. For working up, 100 ml. of water are added to the mixture which is then extracted three times with diethyl ether. The extracts are washed with 10% by weight aqueous potassium bicarbonate solution and with semi-saturated and saturated sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on silica gel with hexane/ethyl acetate (19:1 parts by volume) there is obtained pure 6-[(6-oxo-3-methyl-2-hexenyl)-oxy]-2,3-dihydrobenzofuran which is distilled in a bulb-tube at 100° C./0.02 mmHg.

Provenance & Evidence