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

Participants

Reaction Conditions

Reaction Steps

p-Anisidine (123 g), propionic acid (200 ml) and water (250 ml) were mixed in a 5 liter reaction flask and cooled to 0° C. Sulfuric acid 98% (202 g) was added gradually with cooling followed by the addition of sodium nitrite (69 g) dissolved in 200 ml water over a 50 minute period. The stirring was continued for a further one hour at 0°-2° C., t-Butylamine (0.5 g) was then added. After an additional 15 minutes of stirring Pd(dba)2 (1.0 g) and propionic acid (250 ml) were added. 2-Ethylhexyl acrylate (276 g) was then added over a period of 10 minutes while maintaining the temperature at 0° C. The reaction was then allowed to warm to room temperature and stirred for 24 hours. Sodium hydroxide (333 g of 30% solution) was added and after 10 minutes the lower aqueous layer was separated and extracted twice with ether (200 ml). The ether layers were combined and evaporated. The residue was combined with the organic layer and distilled to give separate fractions of propionic acid, excess ethylhexyl acrylate and 273 g of 2-ethylhexyl p-methoxycinnamate (94.0% yield).

Provenance & Evidence