Hydrochloric Acid → 4-[(1Z)-1-(4-Hydroxyphenyl)-2-phenylbut-1-enyl]benzaldehyde

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Reaction Steps

To a solution of 16 (194 g, 0.42 mol) in EtOH (1.25 L) was added 12 M HCl (250 mL). The reaction mixture was refluxed for 3 h, cooled to RT, and the volatiles were removed under reduced pressure. H2O (750 mL) was added and the mixture was extracted with ether (3×500 mL). The combined ethereal extracts were washed with H2O (750 mL), brine (750 mL), and dried over MgSO4. Concentration followed by recrystallization from hexanes afforded 52.8 g (38%) of 10 as a white solid. 1HNMR (400 MHz, DMSO-d6): δ 0.83 (t, J=7.3 Hz, 3H), 2.33 (q, J=7.3 Hz, 2H), 6.40 (d, J=8.4 Hz, 2H), 6.60 (d, J=8.4 Hz, 2H), 7.10-7.20 (m, 5H), 7.40 (d, J=7.9 Hz, 2H), 7.90 (d, J=8.1 Hz, 2H), 9.23 (s, 1H), 9.98 (s, 1H).

Provenance & Evidence