Hydrochloric Acid → (2E)-3-{4-[(4-Hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-2-propenoic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl(2E)-3-{4-[(4-hydroxyphenyl)(3,3,5,5-tetramethylcyclohexylidene)methyl]phenyl}-2-propenoate (15) (7.75 g, 0.0185 mmol) in THF (100 mL) and EtOH (100 mL) was slowly added 1 N NaOH (93 mL) solution at RT. The reaction mixture was heated to 70° C. and stirred at that temperature for 4.5 h. Reaction mixture was cooled to room temperature and then poured into 20% aqueous HCl (350 mL). The product was separated out as an off-white solid. The suspension was filtered and the filtered solid was dried to afford 6.01 g (83%) of compound 16 as an off-white solid. mp 219-220° C. 1H NMR (300 MHz, DMSO-d6): δ 0.89 (s, 6 H), 0.90 (s, 6 H), 1.27 (s, 2 H), 1.91 (s, 2 H), 1.94 (s, 2 H), 6.47 (d, J=15.9 Hz, 1 H), 6.68 (d, J=8.1 Hz, 2 H), 6.95 (d, J=8.4 Hz, 2 H), 7.16 (d, J=8.1 Hz, 2 H), 7.52 (d, J=15.9 Hz, 1 H), 7.60 (d, J=8.1 Hz, 2 H), 9.31 (s, 1 H), 12.35 (s, 1H). LRMS (ESI): m/z 389 (M−H)−.

Provenance & Evidence