2-ethoxy-4-formylphenyl stearate

DMAP (0.0611 g, 0.5 mmol) and EDC.HCl (1.246 g, 6.5 mmol) was dissolved in acetonitrile (5.0 mL) to create the catalyst. Ethylvanillin (0.8 g, 4.8 mmol) was dissolved in acetonitrile (5.0 mL) and was then added to the catalyst solution. Stearic acid (1.6 g, 5.6 mmol) was partially dissolved in acetonitrile (5.0 mL) and was then added to the catalyst solution. The mixture was then rinsed with acetonitrile (2.0 mL) after each transfer of phenol and carboxylic acid. Initial cloudy suspension was observed. The suspension was then heated under reflux for 1 hour with TLC with UV-visualisation conducted every 20 mins to determine the extent of reaction. After allowing the solution to cool to room temperature, the solution was washed by HCl (20.0 mL, 1 mol) thrice with ethyl acetate (10.0 mL) and brine (10.0 mL). The solution was then washed by NaHCO3 (120.0 mL, 10.0%) twice with ethyl acetate (10.0 mL) and brine (10.0 mL). The solution was further washed by water (20.0 mL) with ethyl acetate (10.0 mL) and brine (10.0 mL) and was then washed with brine (20.0 mL) twice. The aqueous part was collected in a separate flask. The remaining organic layer was treated with MgSO4. MgSO4 was removed via gravity filtration, washing once with hexane (10.0 mL). The ethyl acetate and hexane solvents in the ester filtrate were then removed in vacuo to give a white powder (1.0 g, 2.3 mmol, 48 % yield)