Ethanol → 6-[(7-Ethoxy-3,7-dimethyloctyl)oxy]-3-methyl-2,3-dihydro-1-benzofuran

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Reaction Steps

A solution of 3.48 g. of 6-[(3,7-dimethyl-6-octenyl)-oxy]-3-methyl-2,3-dihydrobenzofuran in 15 ml. of absolute ethyl alcohol is slowly added dropwise at room temperature to a suspension of 3.81 g. of mercuric acetate in 30 ml. of absolute ethyl alcohol. The mixture is thereupon stirred for one hour at room temperature, cooled by means of an ice bath and 12.8 ml. of 10% by weight aqueous hydroxide followed by 0.24 g. of sodium borohydride in 12.8 ml. of 10% by weight aqueous sodium hydroxide are added dropwise. After stirring for 30 minutes at room temperature, the mixture is filtered through diatomaceous earth, the aqueous phase saturated with sodium chloride and subsequently extracted with pentane. The extracts are washed neutral with aqueous sodium chloride solution, dried over sodium sulfate and evaporated. By chromatography on silica gel there is obtained pure 6-[(7-ethoxy-3,7-dimethyl-octyl)-oxy]-3-methyl-2,3-dihydrobenzofuran which is distilled in a bulb-tube at 132° C./0.01 mmHg; nD 22 = 1.4976.

Provenance & Evidence