5-Methoxyindan-1-one → 5-Hydroxy-1-indanone

Participants

Reaction Conditions

Reaction Steps

A solution of 5-methoxy-indan-1-one (4.9 grams, 30 mmol)in 1:1 concentrated HBr/HOAc (150 mL) was heated at 112° C. for 28 hours. The reaction was cooled to 23° C. and filtered through celite. The filtrate was diluted with ethyl acetate (1000 mL) and washed with saturated aqueous NaCl (100 mL), saturated aqueous NaHCO3 (2×100 mL) and with saturated aqueous NaCl (100 mL). The ethyl acetate solution was dried (MgSO4) and concentrated in vacuo to give 1.6 grams of crude product. 1H NMR (250 MHz, d6 -DMSO): d 7.45 (d, 1 H), 6.82 (s, 1 H), 6.78 (d, 1 H), 2.95 (t, 2H), 2.55 (t, 2 H).

Provenance & Evidence