2,3-Dihydro-1,4-benzodioxin-6-ylmethanol

29668-44-8

39270-39-8

General procedure for the synthesis of benzodioxane-6-methanol from 1,4-benzodioxane-6-carboxaldehyde: 2,3-Dihydro-benzo[1,4]dioxine-6-carboxaldehyde [RN 29668-44-8] (3.04 g, 18.54 mmol) was dissolved in ethanol (100 mL) and the solution was cooled to 0 °C. Sodium borohydride (1.41 g, 37.77 mmol) was added to this solution in batches with stirring. The reaction mixture was continued to be stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched by the slow addition of water (10 mL), followed by concentration under reduced pressure to remove the solvent. The residue was separated by extraction with 5% aqueous sodium bicarbonate (20 mL) and dichloromethane (2 x 50 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using a gradient elution of dichloromethane and methanol. Benzodioxane-6-methanol was finally obtained as a colorless oil (3.00 g, 97% yield).