Acetic Acid → HCID 53770526, compound

Participants

Reaction Steps

90 g of 2,4,6-trimethylbenzaldehyde, 150 g of 4-chloroacetoacetic acid ethyl ester, 2.6 ml of piperidine and 7 ml of glacial acetic acid were dissolved in 60 ml of benzene and the solution was boiled for 6 hours using a water separator. 200 ml of ethyl acetate were added to the cooled solution, the solution was extracted in each case once with saturated sodium bicarbonate solution, water and 1 M citric acid solution and the extract was dried over magnesium sulphate and evaporated. The crude product was subjected to incipient distillation under a high vacuum in order to free it from excess 4-chloroacetoacetic acid ethyl ester. After chromatography of the product on Silica gel 60 (Merck, 70-230 mesh), 21 g of the E-isomer could be crystallized with isopropanol and 3:1 Z/E mixture remained as the mother liquor in the form of an oil. Total yield: 39%. E-isomer: melting point 85°.

Provenance & Evidence