Hydrochloric Acid → HCID 22129630, compound

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.

1. stirringthe reaction mixture stirred for another 3 h at room temperature
2. temperaturecooling
3. customThe organic phase was separated
4. extractionthe residual aqueous phase repeatedly extracted with ether
5. washThe combined organic phases are washed with saturated saline solution
6. dry with materialdried over sodium sulfate
7. customevaporated under vacuum
8. customThe residue was crystallized from benzene

ORD record

ord-9883661d2b904f39b98b1c7780faf703

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06147073