4-allyl-2-methoxyphenyl 2-cyclopropylacetate

15 mL acetonitrile, DMAP(61 mg, 0.5 mmol) and EDC.HCl (1.25 g, 6.5 mmol) were mixed. 0.5635 g of cyclopropylacetic acid (5.64 mmol) was added, rinsing with 5 + 2 mL of acetonitrile. 0.837 g of eugenol (5.10 mmol) was added, rinsing with 5 + 2 mL of acetonitrile. The mixture was reacted under reflux at 97–99oC with stirring. TLC was conducted every 20 min with 30% ethyl acetate in hexane as the eluent to see when reaction was complete. At 60 mins the reaction was complete with a colourless solution produced. When complete, after adding 20 mL hexane, the mixture was washed with HCl (1M, 2 x 20 mL), NaHCO3 (10 wt%, 2 x 20 mL), 20 mL distilled H2O and saturated NaCl(aq) (2 x 20 mL). The mixture was filtered under gravity and rinsed with 10 mL hexane after drying with MgSO4. The solvent was then removed in vacuo, leaving our synthesized ester. No visible change to colour after being rotary evaporated. Product not 100% pure