Ethyl 4-chloroacetoacetate → HCID 14372562, compound

Participants

Reaction Steps

Two grams of amberlyst 15 ion exchange resin was added to a solution of 8.23 g (0.05 mol) of ethyl 4-chloroacetoacetate in 25 mL of methyl orthoformate. The solution was stirred overnight, the resin was filtered, and excess ortho ester was removed in vacuo. The residue was then heated slowly over 1 h to 190° C., after which it was allowed to cool and then short path distilled to yield 7.37 g (83%) of ethyl 3-methoxy-4-chlorocrotonate as a colorless liquid: bp 145°-148° C. (40 mm); VPC (6 ft 5% SF 96 on 60-80 mesh chromosorb G; 160° C.; 60 cm3 /min He flow) tR =1.9 min; NMR (CDCl3) 1.10 (t, 3H, J=7 Hz, COOCCH3), 3.73(s, 3H, OCH3), 4.20 (q, COOCH2C, J=7 Hz, COOCH2C), 4.67 (s, 2H, ClCH2), 5.17 (s, 1H, CH).

Provenance & Evidence