Sodium Hydroxide → 4-[Cyclohexylidene(4-hydroxyphenyl)methyl]benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-[cyclohexylidene(4-hydroxyphenyl)methyl]benzoate (156) (0.175 g, 0.54 mmoL) in THF (3 mL) and EtOH (3 mL) was added 1 N NaOH (6 mL) at RT. The reaction mixture was heated between 85-90° C. under a nitrogen atmosphere for 2 h. The oil bath was removed and the reaction mixture was allowed to cool to RT. The reaction mixture was partially concentrated in vacuo to remove the THF and EtOH. The basic aqueous mixture was diluted with H2O and the pH was adjusted to ˜1 (as judged by litmus paper) with 1 N HCl. The acidic aqueous mixture was extracted with CH2Cl2 (2×). The organic extracts were combined, dried (MgSO4), filtered, and the filtrate was concentrated to give the 0.087 g (52%) of compound 157 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 1.53 (m, 6 H), 2.11 (m, 2 H), 2.17 (m, 2 H), 6.67 (d, J=8.5 Hz, 2 H), 6.85 (d, J=8.5 Hz, 2 H), 7.15 (d, J=8.1 Hz, 2 H), 7.84 (d, J=8.3 Hz, 2 H), 9.35 (s, 1 H), 12.81 (br s, 1). LRMS (ESI): m/z 307 (M−H)−.

Provenance & Evidence