Methyl 4-methylcinnamate

Preparation

Using polyethylene glycol (PEG) as a phase transfer catalyst and PdCl2 as the catalyst in a solid-liquid phase, METHYL 4-METHYLCINNAMATE was synthesized in a yield of 73.1%. This reaction exhibits high selectivity and the product is easily separated, making it another good method for the synthesis of METHYL 4-METHYLCINNAMATE.
In a 100 mL four-necked flask equipped with a reflux condenser, thermometer, and dropping funnel, PdCl2 (0.15 mmol), NaHCO3 (37.5 mmol), PEG-800 (5 mmol), and DMF (10 mL) were added. The mixture was heated to 70 °C under nitrogen protection, then cooled to room temperature. Iodobenzene (15 mmol) and methyl methacrylate (30 mmol) were then added through a dropping funnel, and the mixture was heated to 120 °C for 6 h. After filtration, the reaction solution was extracted with water and then with diethyl ether. The solvent in the extract was removed by rotary evaporation. GC analysis showed a yield of 73.1%.

The pure product was obtained by column chromatography (petroleum ether: ethyl acetate = 10:1), and determined by IR, 1H NMR and GC-MS.

Uses

Methyl p-methylcinnamate is a pharmaceutical intermediate used in the synthesis of the antithrombotic drug ozagrel sodium.

Application

Methyl methyl cinnamate has a high ultraviolet light absorption rate and can effectively resist ultraviolet rays in the range of 280~320nm. It is widely used in sunscreen cosmetics, textiles, polymers and pharmaceutical intermediates.

Synthesis Reference(s)

Synthetic Communications, 17, p. 1839, 1987 DOI: 10.1080/00397918708077329