Water → HCID 14566727, compound

Participants

Reaction Steps

A suspension of 7-nitrotetralone (20 g, 0.105 mol) in MeOH (300 mL) was treated with NaBH4 (4.1 g) with intermitent cooling. After the addition, cooling was removed and the reaction stirred over night. The reaction was cooled in ice-water and quenched with a solution of MeOH (200 mL) and concentrated HCl (35 mL). The solvent was evaporated, the residue was suspended in H2O, and the mixture was extracted with CHCl. The extracts were dried and the solvent evaporated to give a tan solid. A mixture of the solid, p-toluenesulfonic acid (0.4 g), and toluene (300 mL) was heated to reflux for over night with water being collected in a Dean-Stark trap. The reaction was cooled, washed with H2O, aqueous NaHCO3, and brine, then the solvent was dried and evaporated to give a dark liquid (15.6 g) that had an nmr consistent with the desired material.

Provenance & Evidence