Hydrochloric Acid → HCID 73853845, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 10.1 g of 4,4-diphenylcyclohex-2-enone in 60 cm3 of tert-butanol is added to a solution of 6.5 g of potassium tert-butoxide in 50 cm3 of tert-butanol at a temperature in the region of 30° C. After stirring for about 15 minutes at a temperature in the region of 30° C., this solution is added dropwise to 14 cm3 of tert-butyl nitrite. The reaction mixture is stirred at a temperature in the region of 20° C. for 2 hours. 100 cm3 of aqueous 3 M hydrochloric acid solution and 100 cm3 of diethyl ether are then added to the preceding mixture at a temperature in the region of 20° C. After separation of the phases by settling, the aqueous phase is extracted with 100 cm3 of diethyl ether. The combined organic phases are washed with three times 100 cm3 of saturated aqueous sodium bicarbonate solution and then with 100 cm3 of saturated aqueous sodium chloride solution, and then dried over magnesium sulphate, filtered and concentrated. After concentrating to dryness under reduced pressure (13 kPa), the residue is purified by flash chromatography on a column of silica (eluent: cyclohexane/ethyl acetate (80/20 by volume)]. 2.23 g of 5,5-diphenylcyclohex-3-ene-1,2-dione 1-oxime are thus obtained in the form of a yellow foam, which is used without further modification for subsequent syntheses and the characteristics of which are as follows:

Provenance & Evidence