2-formyl-6-methoxyphenyl 2-cyclopropylacetate

o-vanillin (0.7 g, 4.60 mmol), cyclopropylacetic acid (0.5 g, 4.99 mmol), EDC.HCl (1.1 g, 5.74 mmol), DMAP (0.1 g, 0.819 mmol) and acetonitrile (32 mL) as the solvent were heated under reflux for 120 min. The reaction mixture was sampled every 20 min and thin layer chromatography with iodine visualisation was used to determine the reaction endpoint. Hexane (20 mL) was used to obtain the product and the organic layer was worked up using 1M hydrochloric acid (2 x 20 mL), 10 wt% sodium bicarbonate (2 x 20 mL), water (20 mL) and finally saturated aqueous sodium chloride (2 x 20 mL). The organic layer was dried using magnesium sulfate and then gravity filtered to remove the magnesium sulfate. Hexane was removed from the organic layer in vacuo to retrieve the product, however no product was found on removal of the hexane. Thus, ethylacetate (39.5 mL) was added to the aqueous washings obtained during the workup on hexane in order to isolate the product. The organic layer was then worked up using 1M hydrochloric acid (19.5 mL) + saturated aqueous sodium chloride solution (10.5 mL), 10 wt% sodium bicarbonate (20.5 mL) + saturated aqueous sodium chloride solution (3 mL) and finally saturated aqueous sodium chloride solution (27 mL). The ethylacetate layer was dried using magnesium sulfate and then gravity filtered to remove the magnesium sulfate. Ethylacetate was removed from the organic layer in vacuo to retrieve the product. The novel ester obtained was weighed : 0.2 g The ester formed crystallised in perfectly round circles after completing the evaporation of ethylacetate in vacuo. These crystals had a light yellow colour