Hydrochloric Acid → HCID 22129630, compound

Participants

Reaction Steps

To a solution of 1,4-dihydroxytetralin (1.640 g, 10 mM), in dichloromethane (50 ml) was added titanium tetrachloride (5.69 g, 30 mM). Then 1,1-dichlorodimethyl ether (1.73 g, 15 mM) was added dropwise under vigorous stirring and the reaction mixture stirred for another 3 h at room temperature. Finally 5% hydrochloric acid (10 ml) was added under ice-cooling. The organic phase was separated and the residual aqueous phase repeatedly extracted with ether. The combined organic phases are washed with saturated saline solution, dried over sodium sulfate and evaporated under vacuum. The residue was crystallized from benzene or alternatively submitted to flash chromatography on silica gel with benzene ethylacetate 85:15, to afford pure title compound in about 60% yield (1.080 g), m.p. 145° C.

Provenance & Evidence