6-Hydroxy-1-indanone

13623-25-1

62803-47-8

6-Methoxy-1-indanone (2.5 g, 15.4 mmol) was slowly added to a stirred suspension of aluminum chloride (5.3 g, 39.7 mmol) in toluene (75 mL) at room temperature and under nitrogen protection. The 6-methoxy-1-indanone remaining in the powder addition funnel was flushed into the reaction mixture using toluene (25 mL). The reaction mixture was heated to reflux and maintained for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and slowly poured into ice water. The mixture was transferred to a dispensing funnel using ethyl acetate. The organic and aqueous layers were separated and the organic phase was sequentially washed twice with water and once with saturated sodium chloride solution, followed by drying with anhydrous magnesium sulfate. The dried organic phase was filtered and the filtrate was concentrated to give 1.5 g (66% yield) of 6-hydroxy-2,3-dihydro-1H-inden-1-one, the product was a light tan solid.1H NMR (400 MHz, DMSO-d6) δ: 9.72 (s, 1H), 7.36 (d, J = 8 Hz, 1H), 7.07 (dd, J = 8, 3 Hz, 1H) , 6.90 (d, J = 3 Hz, 1H), 2.94 (m, 2H), 2.58 (m, 2H).ESI-MS m/z: 149 ([M + H]+).