Hydrochloric Acid → 5,6-Dihydroxy-3,4-dihydronaphthalen-1(2H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution 5,6-dimethoxy-1-tetralone (100 g) in toluene (958 ml) was added aluminum chloride (200 g) in small portions. After the addition was complete the reaction was heated to 80° C. and mechanically stirred for 2 hours. The reaction was cooled and slowly poured into ice and concentrated HCl. The resulting solids were filtered and washed with cold dilute HCl. The resulting solids were taken up into monoglyme, dried (MgSO4), filtered, treated with charcoal, refiltered and concentrated. The residue was co-concentrated with acetonitrile to provide upon cooling 82.5 g of desired product as an off white solid, m.p. 191°-194° C.

Provenance & Evidence