Benzaldehyde → HCID 212553, compound

Participants

Reaction Steps

(66) To a solution of benzaldehyde (430 mg, 4.05 mmol) and 4-chromanone (500 mg, 3.37 mmol) in 8.4 ml of ethanol heated almost to boiling was added 1.7 ml of concentrated hydrochloric acid dropwise. After refluxing for 2 days, the solution was cooled overnight, and a precipitate formed. The precipitate was recrystallized from ethanol to afford 367 mg (46.1%) of white flakes: mp 111.8-113.4° C. (lit. mp 112° C., Powell, J. Am. Chem. Soc., 1923, 45, 2708-2711). 1H NMR (250 MHz) δ 8.06-8.02 (dd, 1H), 7.90 (s, 1H), 7.54-7.31 (m, 6H), 7.09 (t, 1H), 7.00-6.96 (d, 1H), 5.37 (s, 2H), 13C NMR (62.7 MHz) 182.4, 161.3, 137.7, 136.1, 134.6, 131.1, 130.2, 129.7, 128.9, 128.1, 122.1, 118.1, 67.8 ppm.

Provenance & Evidence