Hydrochloric Acid → (1-Oxo-1,3-dihydro-2H-inden-2-ylidene)acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.3 mL of H2SO4 dissolved in 75 mL H2O was added 11.3 g (0.053 mol) of sodium periodate. The reaction mixture was cooled to 0° C. and 8.0 g (0.053 mol) of tartaric acid was added all at once and stirred for 15 min. at room temperature. 5.0 g (0.038 mol) of 1-indanone was added all at once followed by the dropwise addition of 19.0 g (0.24 mol) of 50% NaOH dissolved in 40 mL of H2O. A white precipitate was formed and 75 mL of ethanol was added. The reaction mixture was stirred at room temperature for 1 hour, acidified to pH ~2 with concentrated HCl and stirred for 18 hours at room temperature, filtered and dried to afford 3.3 g of a yellow solid. 1H NMR (CDCl3) δ: 4.08 (s, 2H), 6.54 (s, 1H), 7.4-7.8 (m, 5H).

Provenance & Evidence