4'-Hydroxy-4-biphenylcarbonitrile → 4-(3-Hydroxy-propoxy)-benzoic acid 4'-cyanobiphenyl-4-yl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 2 (10 g, 32.21 mmol), 4′-hydroxy-biphenyl-4-carbonitrile (6.35 g, 32.53 mmol), and toluenesulfonic/4-(dimethylamino)pyridine complex (0.95 g, 3.22 mmol) in anhydrous methylene chloride (100 mL) was added N,N-dicyclohexylcarbodiimide (6.98 g, 33.82 mmol) under argon. The reaction mixture was stirred at 40° C. overnight. Upon filtering off the white residues, the filtrate was diluted with additional methylene chloride. The solution was then washed with water. The silyl ether of the title compound was purified by flash column chromatography on silica gel with gradient elution from 0 to 2% acetone in methylene chloride. The silyl-protected compound was hydrolyzed in tetrahydrofuran: water:acetic acid (80 mL: 80 mL: 240 mL) overnight. The volume of the solution was reduced by 50% via evaporation under reduced pressure. Methylene chloride was added to the slurry for washing sequentially with H2O, a 10% NaHCO3 solution and brine before drying over anhydrous MgSO4. The crude product resulting from evaporation of the solvent was purified by recrystallization from ethanol to yield 3 (10.71 g, 89%). 1H NMR spectral data (400 MHz, CDCl3): δ 2.10 (quintet, 2H, —CH2—), δ 3.95 (t, 2H, —CH2OAr), δ 4.25 (t, 2H, HOCH2—), δ 7.00–8.25 (m, 12H, aromatic rings).

Provenance & Evidence