Ethyl 2-methylacetoacetate → HCID 178422301, compound

Participants

Reaction Steps

A solution of 2.2 g of 4-(4-trifluoromethoxyphenoxy)-3-methyl-aniline, 2.6 g of ethyl 2-methylacetoacetate, and 1.52 g of p-toluenesulfonic acid dissolved in 81 mL of xylene was heated under reflux for 12 hr. This reaction solution was cooled, and the precipitated crystals were then collected by filtration and were washed with distilled water and n-hexane to give 3.88 g of a mixture of 6-(4-trifluoromethoxyphenoxy)-4-hydroxy-2,3,5-trimethyl-quinoline with 6-(4-trifluoromethoxyphenoxy)-4-hydroxy-2,3,7-trimethyl-quinoline (yield 100%). The crystals of the mixture (2.9 g) thus obtained were stirred in 30 mL of acetic anhydride with heating at 120 to 125° C. for 2 hr. The reaction solution was concentrated, ethyl acetate was then added to the concentrate, and the mixture was washed with saturated brine. The solvent was then removed under the reduced pressure, and the crude product was purified by column chromatography on silica gel (BW300, manufactured by Fuji Sylysia Chemical Ltd., solvent: n-hexane/ethyl acetate) to give 0.4 g of 4-acetoxy-6-(4-trifluoromethoxyphenoxy)-2,3,5-trimethyl-quinoline (yield 12.4%) and 0.19 g of 4-acetoxy-6-(4-trifluoromethoxyphenoxy)-2,3,7-trimethyl-quinoline (yield 6%).

Provenance & Evidence