Sulfuric Acid → HCID 21951266, compound

Participants

Reaction Conditions

Reaction Steps

5 g (131 mmol) of sodium borohydride and 21 g (80 mmol) of 2,5,6,7-tetramethyl-4-(4′-tert-butylphenyl)-1-indanone (3d) together with 200 ml of toluene were placed in a reaction vessel. At 50° C., 25 ml of methanol were added slowly and the reaction mixture was stirred at 50° C. for 3 hours. After cooling to room temperature, 35 ml of 2 N sulfuric acid were added and the mixture was stirred for 30 minutes. After phase separation, the organic phase was washed twice with a total of 60 ml of 2 N sulfuric acid, most of the solvent was removed and the residue was taken up in 200 ml of toluene and admixed with 0.2 g of p-toluenesulfonic acid. Water was distilled off from this reaction mixture by refluxing for 1.5 hours on a water separator until reaction was complete. The reaction mixture was washed once with 100 ml of saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. After removal of the solvent, the residue was dried in an oil pump vacuum. Crude product was purified by recrystallization in heptane. This gave 9.0 g of (3e).

Provenance & Evidence