Synthetic Route of 24131-31-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.24131-31-5, name is (3,5-Bis(benzyloxy)phenyl)methanol, molecular formula is C21H20O3, molecular weight is 320.3817, as common compound, the synthetic route is as follows.
General procedure: 3-Hydroxybenzaldehyde (5.00 g, 0.041 mol) was dissolved in anhydrous acetonitrile (130 mL) under argon atmosphere. Cesium carbonate (20.01 g, 0.061 mol) was added and the suspension stirred for 5 min. Benzyl bromide (11.69 mL, 0.102 mol) was then added and the solution heated at reflux for 16 h. The solution was concentrated on rotary evaporator, water was added and the mixture was extracted with EtOAc. The organic phase was washed twice with water, once with brine, dried over MgSO4, filtered and concentrated. Water was added and the mixture was extracted with CH2Cl2. The crude product was purified by flash chromatography on silica gel with hexanes/EtOAc (80/20) to yield 3a as a white solid (8.59 g). 1H NMR delta (CDCl3) 5.13 (s, 2H, PhCH2O), 5.33 (s, 2H, COOCH2Ph), 7.35-7.50 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O), 10.00 (s, 1H, PhCHO). The aldehyde 3a was dissolved in anhydrous THF (200 mL) under argon and cooled to 0 C. Lithium aluminum hydride (1.55 g, 0.041 mol) was added in small portions and the solution stirred at room temperature for 2 h. The reaction was then quenched using water (0.8 mL), a 10% wt aqueous NaOH solution (1.15 mL) and water again (1.9 mL) and left to settle. The suspension was then filtered and concentrated. Water was added and the mixture extracted with EtOAc, the organic phase dried over MgSO4, filtered and concentrated to yield 7.07 g crude alcohol 3b. 1H NMR delta (CDCl3) 4.68 (s, 2H, PhCH2OH), 5.08 (s, 2H, PhCH2O), 6.90-7.46 (m, 9H, 2-CH, 4-CH, 5-CH, 6-CH and PhCH2O). Crude alcohol 3b (7.06 g) was dissolved in anhydrous CH2Cl2 (330 mL) and the solution cooled to 0 C. Triphenylphosphine (17.28 g, 0.066 mol) and carbon tetrabromide (21.85 g, 0.066 mol) were then added and the solution stirred at room temperature for 2 h. The reaction mixture was quenched with water and extracted with CH2Cl2. The organic phase was dried over MgSO4, filtered and concentrated. The product was purified by flash chromatography on silica gel with hexanes/EtOAc (9/1) to yield 5.85 g (64%) of bromide 3c.
Statistics shows that 24131-31-5 is playing an increasingly important role. we look forward to future research findings about (3,5-Bis(benzyloxy)phenyl)methanol.
Reference:
Article; Fournier, Diane; Poirier, Donald; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4227 – 4237;,
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