Ethanol → HCID 22057751, compound

Participants

Reaction Steps

To the solution of 2-ethyl-biphenyl-4-carbonitrile (0.95 g, 4.58 mmol) in ethanol (50 mL) is added solid KOH (2.56 g, 45.8 mmol). The resulting mixture is heated at reflux for 12 h. After cooling to room temperature, the solvent is evaporated to dryness under reduced pressure. H2O (100 mL) is added and aqueous HCl (2N) is slowly added until the pH is adjusted to ca. pH=1. The mixture is extracted with EtOAc (3×50 mL). The combined organic layers are washed with saturated aqueous NaCl, dried over Na2SO4, and concentrated. The obtained crude 2-ethyl-biphenyl-4-carboxylic acid is dissolved in methanol (20 mL). Concentrated aqueous HCl (5 mL) is added and the mixture is heated at reflux for 4 h. After cooling to room temperature, the reaction mixture is concentrated under reduced pressure. The residue obtained is dissolved in diethyl ether and washed with saturated aqueous NaHCO3 (3×10 mL). The organic layer is separated and dried over Na2SO4 After concentration, the crude 2-ethyl-biphenyl-4-carboxylic acid methyl ester is dissolved in THF (5 mL) and added dropwise to the mixture of LAH (200 mg, 5.2 mmol) in THF (15 mL, anhydrous) at 0° C. After 1 h, the reaction is quenched by the slow addition of H2O, followed by the addition of aqueous HCl (1N, 20 mL). The mixture is extracted with EtOAc (3×40 mL). The combined organic layers are washed with saturated aqueous NaHCO3, saturated aqueous NaCl, and dried over Na2SO4. After concentration, the crude product is purified by silica gel chromatography (20% EtOAc in hexanes) to give (2-ethyl-biphenyl-4-yl)-methanol as a colorless oil.

Provenance & Evidence