Methanol → HCID 22915493, compound

Participants

Reaction Steps

To a solution of 4-(4′-cyanobiphenyl-4-yloxy)butyric acid ethyl ester (3.78 g, 12.7 mmol) in THF (50 ml) was added a solution of NaOH (1.0 g, 25 mmol) in water (1.5 ml). The mixture was stirred at room temperature for 1.5 h and then at 67° C. for 3 h. More NaOH (1 g) in water (1 ml) was added, and stirring at room temperature was continued for 15 h. MeOH (10 ml) was added, and after stirring at room temperature for 1.5 h the mixture was diluted with water (150 ml) and acidified with concentrated, aqueous HCl (6.6 ml). The product was isolated by filtration and washed with water (approx 20 ml). The solid was suspended in MeCN (50 ml), heated to reflux (no dissolution) and allowed to cool to room temperature. Filtration and drying under reduced pressure yielded 2.70 g (76%) of 4-(4′-cyanobiphenyl-4-yloxy)butyric acid as a colorless solid.

Provenance & Evidence