1-cyclobutylidenepropan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:35.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.75 g Sodium added in portions to 240 ml of methanol and the solution is heated to reflux for 1 hour. 28.4 ml Dimethylmalonate are added and the mixture is heated to reflux for another 10 minutes. The mixture is cooled to 35° C., 350 g 1-cyclobutylidenepropan-2-one (7% in 1,2-dichlorobenzene) are added and the mixture is refluxed for 1 hour. After recooling to room temperature a solution of 28.0 g potassium hydroxide in 130 ml water are added and the mixture is refluxed for 1 hour. The mixture is cooled to room temperature, the pH is adjusted to 1.5 by careful addition of half saturated hydrochloric acid and it is refluxed for 1 hour. The mixture is cooled to room temperature and the aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, concentrated in vacuo and the residue is purified by chromatography on silica gel (petroleum ether/ethyl acetate 50:50). the solution is heated to reflux for 1 hour the mixture is heated to reflux for another 10 minutes the mixture is refluxed for 1 hour After recooling to room temperature are added the mixture is refluxed for 1 hour The mixture is cooled to room temperature is refluxed for 1 hour The mixture is cooled to room temperature the aqueous phase is extracted with ethyl acetate The combined organic phases are dried over sodium sulfate concentrated in vacuo the residue is purified by chromatography on silica gel (petroleum ether/ethyl acetate 50:50)