Potassium Hydroxide → Ethyl 3-oxovalerate

Participants

Reaction Steps

50 g of 4-(β-methoxyethoxy)-aniline in 76.5 ml of strong hydrochloric acid and 50 ml of water are diazotized at 0° C. by the dropwise addition of a solution of 22.8 g of sodium nitrite in 70 ml of water. The reaction mixture is stirred for 1 h whereupon 32 g of sodium acetate are added. Then a solution of 47.5 g of α-methylacetylacetic acid ethyl ester in 300 ml of ethanol is prepared, to which a solution of 21.6 g of potassium hydroxide in 30 ml of water is added dropwise at 0° C. Then successively 300 g of ice and the diazonium solution are added, whereupon the mixture is stirred for another 4 h. The mixture is shaken out with toluene, whereupon the toluene is evaporated. Yield: 77.5 g of a reddish brown oil, which is transformed without any further purification.

Provenance & Evidence