(3-ethoxyphenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a mixture of 3-ethoxybenzyl alcohol (4.15 g) and toluene (50 ml) were added one drop of pyridine and thionyl chloride (3.0 ml), and the resulting mixture was stirred at room temperature for one hour. The reaction mixture was diluted with ethyl acetate, washed successively with water, an aqueous saturated solution of sodium bicarbonate, water and an aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 3-ethoxybenzyl chloride (5.34 g) as an oil. washed successively with water an aqueous saturated solution of sodium bicarbonate, water and an aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate The resulting organic layer was evaporated under reduced pressure to remove the solvent

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

Procedure: To a mixture of 3-hydroxybenzyl alcohol (3.56 g) and acetone (100 ml) were added iodoethane (6.7 g) and potassium carbonate (7.9 g), and the resulting mixture was heated at reflux for 61 hours. The reaction mixture was concentrated, ethyl acetate was added to the residue and the resulting mixture was washed successively with water and an aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 3-ethoxybenzyl alcohol (4.15 g) as an oil. the resulting mixture was heated at reflux for 61 hours The reaction mixture was concentrated ethyl acetate was added to the residue the resulting mixture was washed successively with water an aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate The solvent was evaporated under reduced pressure