Dimethylformamide → 1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Phosphorus oxychloride (25.82 mL, 0.277 mol) was added dropwise to a solution of trichloroethylene (62.5 mL) and DMF (25.48 mL, 0.329 mol) keeping the temperature between 5°-10° C. -Tetralone (40 g, 0.274 mol) in trichloroethylene (62.5 mL) was added dropwise. The reaction mixture was stirred at 60° C. for 3 hours and at room temperature overnight. An aqueous sodium acetate solution (100 g/300 mL H2O) was added dropwise while cooling in a water bath. The aqueous phase was extracted with ether (3×200 mL), dried (MgSO4) and concentrated to give an oil (50 g). 20 g of this crude oil was chromatographed on silica gel with 50% ethyl acetate/hexane to yield 9.95 g (50%) of pure product as a white solid, m.p. 37° C.

Herkunft & Nachweise