Sulfuric Acid → 3,3,6-Trimethyl-2,3-dihydro-1H-inden-5-ol

Participants

Reaction Steps

Compound 135 was prepared by the catalytic hydrogenation (40 psi.) of 5-hydroxy-3,3,6-trimethyl-1-indanone (134) (1.54 g, 8.1 mmol) in methanol (13 mL) followed by the addition of sulfuric acid (169 μL). The content was degassed several times with nitrogen before palladium-on-charcoal (10%) was added. The hydrogenation was allowed to react overnight under hydrogen pressure. The reaction content was filtered through celite then brought to dryness. The residue was redissolved in diethyl ether, neutralized with sodium bicarbonate (10%) and washed with water and brine. 3,3,6-Trimethyl-5-indanol was purified with ethyl acetate and hexane (3%, 10% and 30%) to obtain 0.91 g of light yellow solid. (64% yield) Ref. Qd419-161, Wilt, J. W.; Schneider, C. A.; J. Org. Chem, 1961, 26, 4196. 1H NMR (300 MHz, CDCl3) δ 6 1.22 (s, 6H), 1.94 (dd, 2H, J=7.37, 6.99 Hz), 2.25 (s, 3H), 2.54 (s, 3H), 2.56 (s, 3H), 2.85 (d, 2H, J=7.18 Hz), 3.89 (s, 3H), 5.31 (d, 1H, J=3.59 Hz), 6.31 (s, 1H), 6.84 (s, 1H), 6.99 (bs, 1H), 7.07 (s, 1H), 7.16 (d, 1H, J=3.59 Hz), 8.33 (bs, 1H).

Provenance & Evidence