Methane → 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

Participants

Reaction Steps

A mixture of 4.68 g (20 mmol) of p-iodoanisole, 4.05 g (22 mmol) of 2-ethylhexyl acrylate, 2.22 g (22 mmol) of triethylamine, 1.32 g (22 mmol) of acetic add and 15 mg of palladium of charcoal (5%) is stirred at 150° C. After one hour it is established by gas chromatography that the reaction has been completed. The mixture is then treated at about 80° C. with water and toluene and the catalyst is filtered off. The organic phase is washed in sequence with 2N hydrochloric acid and water, dried over anhydrous sodium sulphate and concentrated under reduced pressure. After distillation there is obtained pure 2-ethylhexyl p-methoxycinnamate, b.p. about 185° C./0.3 Torr. The yield is 92% of theory. 1H-NMR (CDCl3, 200 MHz): 0.86-0.98 ppm (m, 6H), 1.25-1.72 ppm (m, 9H), 3.84 ppm (s, 3H), 4.11 ppm (d, 6 Hz, 2H), 6.32 ppm (d, 15.5 Hz, 1H), 6.85-6.95 ppm (duplettoid m, 1H), 7.44-7.54 ppm (duplettoid m, 1H), 7.64 ppm (d, 15.5 HZ, 1H).

Provenance & Evidence