3-[4-(Benzyloxy)phenyl]acrylic acid

Synthesis

7400-08-0

100-39-0

6272-45-3

GENERAL STEPS: To 4-hydroxycinnamic acid (7 g, 42.6 mmol) was added anhydrous ethanol (40 mL) and stirred until completely dissolved to form a clarified solution. Subsequently, benzyl bromide (15 g, 10.6 mL, 87.7 mmol) and aqueous sodium hydroxide (8.5 g, 212 mmol, dissolved in 40 mL of distilled water) were added sequentially and stirred for 5 minutes to ensure homogeneous mixing. The reaction mixture was placed in a reflux unit and refluxed continuously for 36 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete conversion of 4-hydroxycinnamic acid, the reaction mixture was cooled in an ice bath. Subsequently, the cooled ethanol reaction mixture was slowly poured into a 1-liter beaker containing crushed ice and carefully acidified with 5N hydrochloric acid to the proper pH to induce precipitation of solid compounds. The precipitate was collected by filtration, washed with plenty of water to remove impurities and finally dried to give the white solid product (E)-3-(4-(benzyloxy)phenyl)acrylic acid (10.3 g, 95% yield).

References