Sodium Hydroxide → 2'-(2-Methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

At ambient temperature, to a stirred mixture of silver (I) oxide (0.570 g, 2.46 mmol) in H2O (9.8 mL) was added NaOH (0.983 g, 24.6 mmol) and the reaction was heated at 50° C. After 0.5 h, to the reaction was added a solution of 2'-(2-methoxyethoxymethoxy)-[1,1';3',1"]terphenyl-5'-carbaldehyde (1.78 g, 4.92 mmol) in THF (9.8 mL) and the reaction was heated at 90° C. for 1 h. To the reaction was added silver (I) oxide (0.570 g, 2.46 mmol), NaOH (0.983 g, 24.6 mmol) and H2O (10.0 mL). The reaction was heated at 90° C. for 16 h. The reaction was filtered through a celite pad, rinsing with hot H2O (3×). The filtrate was washed with ether (3×), acidified with 2N HCl (pH 2) and extracted with EtOAc. The organic extracts were dried (MgSO4) and concentrated to give 1.73 g (93%) of the title compound. 1H NMR (DMSO-d6) δ 2.77-2.80 (m, 2 H), 2.88-2.91 (m, 2 H), 3.01 (s, 3 H), 4.39 (s, 2 H), 7.39-7.52 (m, 6 H), 7.59-7.62 (m, 4 H), 7.89 (s, 2 H), 13.07 (s, 1 H).

Provenance & Evidence