Tetrahydrofuran → 4-[(4,4-Dimethyl-cyclohexylidene)-(4-hydroxy-phenyl)-methyl]-benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of THF (2 mL) and ethanol (2 mL) containing 4-[(4,4-dimethyl-cyclohexylidene)-(4-hydroxy-phenyl)-methyl]-benzoic acid methyl ester (171) (0.16 g, 0.457 mmol) was added 1 N NaOH (4 mL). The reaction mixture was heated at 65° C. for 4 h. The reaction mixture was partially concentrated to remove the EtOH and THF. To the basic aqueous mixture was added 1 N HCl to pH˜1 (according to litmus paper). The acidic aqueous solution was extracted with dichloromethane and the organic extract washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was triturated with dichloromethane, filtered, and dried to give 0.132 g (85%) of the title compound 172 as a white powder. 1H NMR (400 MHz, DMSO-d6): δ 0.93 (s, 6 H), 1.32 (s, 4 H), 2.12-2.19 (m, 4 H), 6.66 (d, J=8.3 Hz, 2 H), 6.84 (d, J=8.4 Hz, 2 H), 7.14 (d, J=8.1 Hz, 2 H), 7.83 (d, J=8 Hz, 2 H), 9.33 (s, 1 H), 12.74 (s, 1 H). HRMS (ESI) Calcd for C22H23O3: 335.1647 (M−H)−. Found: 335.1640.

Provenance & Evidence