Hydrochloric Acid → 6-Hydroxy-1-indanone

Participants

Reaction Steps

6-Hydroxyindan-1-one (16) was prepared by the demethylation of 6-methoxyindan-1-one (Rf=0.50, 30% ethyl acetate in hexane) using an approach similar to that of Gates (Gates, M.; Dickinson, C. L., Jr. J. Org. Chem. 1957, 22, 1398). Aluminum bromide (3.35 g, 12.6 mmol) was weighed under argon in an oven-dried flask and 6-methoxyindan-1-one (0.972 g, 6 mmol) was added to it. Dry benzene (40 mL) was added dropwise to this mixture and the resulting reddish-yellow solution was refluxed for four hours. The reaction mixture was cooled to room temperature after TLC showed no more starting material and 30 mL of 6N hydrochloric acid solution was added dropwise. The mixture was heated gently till the resulting solution was homogenous. The benzene layer was removed and the aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with water (50 mL), saturated sodium chloride solution (50 mL), dried over sodium sulfate and filtered. The filterate was removed under reduced pressure to yield 16 (3.41 g, 92%) as a grey solid (Rf=0.33, 30% ethyl acetate in hexane). White needles of compound 16 were obtained upon recrystallization from benzene. 1H NMR (acetone-d6, 200 MHz): 8.62 (s, 1H, D2O exchangeable), 7.39 (dd, J=8 Hz, 1 Hz, 1H), 7.14 (dd, J=8 Hz, 2 Hz, 1H), 7.03 (d, J=2 H z, 1H), 3.01 (m, 2H), 2.58 (m, 2H). EI-MS: 148 (M+, 100%), 120 (M+ -CO, 93%), 92 (M+ -CO--2CH2, 12%).

Provenance & Evidence