Reaction #1929064

Reaction equation

3-hydroxybenzylalcohol

sodium hydroxide

propargyl bromide

xylene

citric acid

→

3-propargyloxybenzyl alcohol

Solvents

THF

water

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was heated
2. 2
   Temperatureat reflux for 6 hours
3. 3
   Otherthe solvent was removed under vacuum
4. 4
   ExtractionThe residue was extracted with ethyl acetate (3×15 mL)
5. 5
   Washthe combined organic layers were washed with saturated NaCl solution (10 mL)
6. 6
   Dryingdried over MgSO4
7. 7
   Concentrationconcentrated

Procedure

To a solution of 3-hydroxybenzylalcohol (2.4 g, 20 mmol) in THF (50 mL) and water (2.5 mL) was first added powdered sodium hydroxide (1.5 g, 37.5 mmol) and then a solution of propargyl bromide, dissolved as an 80% weight solution in xylene (3.36 mL, 30 mmol). The reaction mixture was heated at reflux for 6 hours. To the mixture was added 10% citric acid (2.5 mL) and the solvent was removed under vacuum. The residue was extracted with ethyl acetate (3×15 mL) and the combined organic layers were washed with saturated NaCl solution (10 mL), dried over MgSO4 and concentrated to give the 3-propargyloxybenzyl alcohol.

Source