Hydrochloric Acid → 4,7-dimethyl-1H-indene

Participants

Reaction Conditions

Reaction Steps

2.9 g (0.0181 moles) of 4,7-dimethyl-1-indanone (formula XVII) obtained as described above, are slowly added to a suspension of 0.350 g (0.0692 moles) of LiAlH4 in 30 ml of ethyl ether, maintained at −30° C. in an inert atmosphere. The reaction is complete after 30 minutes. Ice and HCl 2N are cautiously added until acidification, the mixture is then extracted with ethyl ether, and the organic phase is subsequently separated and washed until neutrality. It is anhydrified on sodium sulfate and evaporated, obtaining a residue essentially consisting of 4,7-dimethyl-1-indanol. The residue is dissolved in 10 ml of THF, a pinch of p-toluenesulfonic acid is added and the mixture is brought to reflux temperature for 1 hour. Solid NaHCO3 and Na2SO4 are then added. The mixture is filtered and the solvent evaporated obtaining 2.4 g of 4,7-dimethyl-indene (XVIII) (91% yield).

Provenance & Evidence