Dimethyl Carbonate → HCID 178499032, compound

Participants

Reaction Steps

5-Bromo indanone (8 g, 37.9 mmol) was added to an ice cold solution of sodium hydride (2.72 g, 113.3 mmol) in THF (100 mL) and stirred at room temperature for 30 min. Dimethyl carbonate (17.25 g, 189.56 mmol) was then added and mixture was refluxed for 16 h. Reaction mixture was cooled to room temperature and poured into ice water. pH of solution was made basic using saturated aqueous solution of NaOH solution and extracted with twice with ethyl acetate and concentrated under vacuum. Residue obtained was dissolved in diethyl ether and cooled to 0° C. A solution of saturated aqueous solution of NaOH was added (10 mL) while stirring. Resulting sodium salt was collected by filtration and dried under vacuum to afford crude title compound (7 g) as solid. 1H NMR (400 MHz, DMSO-d6): δ 7.52 (s, 1H), 7.40 (m, 1H), 7.34 (m, 1H), 3.52 (s, 3H), 3.3 (s, 2H).

Provenance & Evidence