Ethyl Acetate → Methyl 4-(3-oxoprop-1-en-1-yl)benzoate

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Reaction Steps

A solution of 27.3 g (0.09 mole) of formyl methyltriphenyl phosphonium bromide and 14.8 g (0.09 mole) of p-carbomethoxybenzaldehyde in 900 ml of dry toluene was refluxed under nitrogen for 24 hours. After evaporating toluene under reduced pressure, the residue was chromatographed over silica column with 5% ethyl acetate in petroleum ether as eluant. The second fraction obtained by using 10% ethyl acetate in petroleum ether gave 4-carbomethoxycinnamaldehyde. Recrystallization from benzene gave 12.5 g 4-carbomethoxycinnamaldehyde, yield 73% m.p. 99°-101° C. The infrared spectrum showed absorption at 1720 cm1 (COOCH3), 1680 cm-1 (CHO), and 1620 cm-1 (--CH=CH--). NMR (CDCl3) showed δ3.8 (s, --COOCH3, 3) 6.5-7.1 (m,=CH--CHO, 1), 7.3-7.6 (m, aromatic, 4), 7.9-8.1 (d, --CH=, 1), and 9.8 (d, --CHO, 1 ). Analysis calculated for C11H10O3 :C, 69.42%, H, 5.2%. Found: C, 68.69%, H, 5.26%.

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