Synthesis
GENERAL PROCEDURE: To a 25 mL round-bottomed flask was added p-chlorobenzaldehyde (1.00 mmol), methyl acrylate (0.130 g, 1.50 mmol), triethylamine (0.152 g, 1.50 mmol) and N,N-dimethylformamide (DMF, 5 mL). DMF solution containing catalyst (catalyst concentrations of 0.1, 0.01 and 0.001 mol%, see Table 1; 0.01 mol%, see Table 2) was added to the above mixture via syringe. The flask was assembled to a water condenser with an anhydrous calcium chloride drying tube, and the reaction mixture was continuously stirred and heated in an oil bath at 90°C for 3 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature and subsequently poured into distilled water (300 mL). The product in the aqueous phase was extracted with ethyl acetate (5 x 50 mL). The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product as an oil. Purification of the crude product by silica gel column chromatography (eluent hexane/ethyl acetate, gradient from 10/0 to 8/2, v/v) gave methyl 3-(4-formylphenyl)acrylate as shown in Tables 1 and 2.
References
[1] Journal of Organic Chemistry, 2011, vol. 76, # 19, p. 8036 - 8041
[2] Polyhedron, 2018, vol. 151, p. 313 - 322
[3] Tetrahedron Letters, 2011, vol. 52, # 37, p. 4782 - 4787
[4] New Journal of Chemistry, 2016, vol. 40, # 2, p. 1250 - 1255
[5] ChemCatChem, 2013, vol. 5, # 8, p. 2418 - 2424
