4-Propoxyphenol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 4-propoxyphenol (10.0 g) and potassium carbonate (10.0 g) in DMF (50 ml) was added bromoacetaldehydedimethylacetal (12.2 g), and the mixture was refluxed for 14 hours and cooled. To the mixture was added water, and the mixture was extracted with ethyl acetate (twice). The organic layer was washed with 1N sodium hydroxide solution (twice) and then washed with saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography to give yellow oil of 4-(2,2-dimethoxy)ethoxypropoxybenzene (12.2 g). the mixture was refluxed for 14 hours cooled the mixture was extracted with ethyl acetate (twice) The organic layer was washed with 1N sodium hydroxide solution (twice) and then washed with saturated brine dried with magnesium sulfate Under reduced pressure, the solvent was evaporated the residue was purified with silica gel column chromatography