Potassium Iodide → Dibenzyl ether

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3,5-dimethyl-4-hydroxybenzoate represented by Formula 146 (1.72 g, 9.52 mmol), 1-bromobutane (1.13 mL, 10.47 mmol), potassium carbonate (K2CO3, 1.45 g, 10.47 mmol) and potassium iodide (KI, 158 mg, 0.95 mmol) in DMF (20 mL) was agitated at 80° C. for 24 hours. After decreasing a temperature of the reaction mixture to room temperature, solids were removed through filtration (and washed with acetone) to obtain a filtrate. After adding ethyl acetate to the filtrate, the solution was consecutively washed with water and a 5N HCl solution. After separating an organic layer and drying the same with magnesium sulfate (MgSO4), the solvent was removed under reduced pressure to prepare a concentrate mixture. This mixture was subjected to separation and purification through column chromatography (ethyl acetate/hexane, 1:5, v/v) using silica gel (SiO2), resulting in a benzylether compound represented by Formula 147 as a desired product (2.1 g, 93%). Analysis data of the product is provided as follows:

Provenance & Evidence