Water → HCID 11084333, compound

Participants

Reaction Steps

To a solution of sodium ethoxide (20.0 g, 0.20 mole) in ethanol (600 ml), a solution of 2-tetralone (42.4 g, 0.29 mole) in ethanol (100 ml) was added dropwise at 0° C. with stirring, then p-toluenesulfonylazide (59.2 g, 0.3 mole) was added dropwise at -15° C. or below to the mixture and reacted with stirring for 3 hours at -10° to 0° C. The reaction mixture was poured into H2O (1 l), extracted with methylene chloride (500 ml×2), the organic layer separated was washed with H2O (500 ml×3), dried over anhydrous MgSO4 and evaporated. The oily residue (72 g) was chromatographed on silica gel (Wakogel C-200) with n-hexane-n-hexane/methylene chloride (1/1) as eluent and recrystallized from n-hexane to afford 6.0 g of 1-diazo-2-tetralone as yellow crystals. m.p. 42.5°-44.2° C.

Provenance & Evidence