Tetrahydrofuran → HCID 13076864, compound

Participants

Reaction Steps

A solution of methyl 5-chlorosalicylate in 200 ml of anhydrous ether was added dropwise with stirring at 10° C. to a mixture of 250 ml of a tetrahydrofuran solution titrating 2.6 M/liter of ethenyl magnesium chloride and 300 ml of anhydrous ether and the mixture was allowed to return to room temperature and was then stirred overnight at room temperature. The mixture was poured into a liter of iced water containing 10% of ammonium chloride and the decanted aqueous phase was extracted twice with 150 ml of ether. The organic extracts were washed 3 times with 100 ml of water, dried over magnesium sulfate, treated with activated carbon and was filtered. The filtrate was evaporated to dryness under reduced pressure and the 39 g of oil residue was chromatographed under pressure over silica gel H. Fractional elution with methylene chloride and evaporation of the solvent yielded 13.9 g of 5-chloro-α,α-bis-ethenyl-2-hydroxybenzene-methanol.

Provenance & Evidence