HCID 10655655, compound → HCID 20095725, compound

Participants

Reaction Steps

41.1.14 ml of a sulphuric acid/nitric acid 65% 1:1 mixture was slowly added dropwise to a solution of 20 g of 3'4'-dihydro-spiro[cyclopentane-1,2'(1'H)-naphthalen]-1'-one in 60 ml of sulphuric acid. After stirring for 2 hrs. at RT the mixture was poured on to 200 g of ice, extracted with ether, washed with a saturated aqueous NaHCO3 solution and with water, dried on Na2SO4, filtered, concentrated and chromatographed over silica gel with cyclohexane/ethyl acetate 9:1. Yield: 12.7 g (52%). A sample was recrystallized from hot isopropyl ether and gave 7'-nitro-3'4'-dihydro-spiro[cyclopentane-1,2'(1'H)-naphthalen]-1'-one as white crystals; m.p. 69°-70° C.

Provenance & Evidence