Sulfuric Acid → HCID 54467755, compound

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Reaction Steps

21.1 g of (6-chloro-7-amino-1,1,3,3-tetramethyl-5-indanyl) methyl ketone are introduced into 48 ml of concentrated sulphuric acid and, after the warming to 50° C., the mixture is treated slowly with 140 ml of distilled water. After cooling down to 0°-5° C., there is introduced dropwise into the mixture over a period of 45 minutes a solution of 5.5 g of sodium nitrite in 20 ml of water. The resulting cold mixture is introduced dropwise while stirring over a period of 2 hours into a solution, held at 70° C., of 60 ml of water and 60 ml of concentrated sulphuric acid. The mixture is cooled, then introduced into ice-water and extracted three times with ether. The organic phase is washed with a sodium chloride solution, dried over sodium sulphate and freed from solvent under reduced pressure. The residue is purified by adsorption on silica gel using hexane/ether (19:1) for the elution. The (6-chloro-7-hydroxy-1,1,3,3-tetramethyl-5-indanyl) methyl ketone obtained from the eluate melts at 78°-80° C. after recrystallisation from hexane/ether.

Provenance & Evidence