Sodium Cyanide → 5-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one

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Reaction Conditions

Reaction Steps

5,6-Dimethoxy-1-indanone (1 g, 5.20 mmol) and NaCN (2.55 g, 52 mmol) were combined in DMSO (10 mL). The reaction was stirred at 100° C. for two days, cooled, diluted with water and extracted with dichloromethane. The aqueous solution was acidified with concentrated HCl, and extracted with dichloromethane. The organic layer was dried over MgSO4 and evaporated to give the title compound (500 mg). MS (DCI/NH3) m/z: 178.99 (M+H)+. 1H NMR (500 MHz, CD2Cl2) δ ppm 2.59 (t, J=5.62 Hz, 2H) 3.01 (t, J=5.62 Hz, 2H) 3.93 (s, 3H) 6.33 (s, 1H) 6.95 (s, 1H) 7.17 (s, 1H).

Provenance & Evidence