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

Participants

Reaction Conditions

Reaction Steps

12.3 g of 4-anisidine (4-methoxyaniline) are mixed while stirring with 10 ml of concentrated sulphuric acid and 60 ml of 2-ethylhexanol and the mixture is cooled to about 10° C. Subsequently 11.7 g of amyl nitrite are added and after addition is complete the mixture is stirred for a further 40 minutes. The reaction mixture is subsequently admixed with 20.2 g of 2-ethylhexyl acrylate and 100 mg of Pd (5% Pd on activated carbon) and heated to 65° C. over a period of 1 hour and stirred for a further 12 hours at this temperature. The mixture is diluted with 100 ml of water and extracted with 200 ml of dichloromethane. As examination by thin-layer chromatography and gas chromatography shows, 2-ethylhexyl p-methoxycinnamate has not been formed in even the smallest amounts. The 2-ethylhexyl acrylate employed is essentially present in unchanged form.

Provenance & Evidence