Sulfuric Acid → 1,3,3-Trimethyl-3,4-dihydroisoquinoline

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Reaction Steps

To a concentrated sulfuric acid (10 ml) was added a solution of 2-methyl-1-phenylpropan-2-ol (7.0 g) and acetonitrile (1.62 ml) in benzene (7.0 ml) dropwise at 0° C. and the mixture was stirred for 24 hours at room temperature. The reaction mixture was neutralized by adding dropwise to a mixture of ice and a saturated aqueous solution of sodium bicarbonate and the mixture was extracted with ethyl acetate twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in ether and thereto was added a 5N aqueous solution of sodium hydroxide and was extracted with 1N hydrochloric acid and a 2N hydrochloric acid. The extract was washed with ether and thereto was added a 5N aqueous solution of sodium hydroxide and was extracted with ether twice. The extract was washed with water and brine successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (2.53 g) having the following physical data.

Provenance & Evidence