Hydrochloric Acid → HCID 59518507, compound

Participants

Reaction Conditions

Reaction Steps

Alternatively, the compounds of formula (V) can be prepared according to a second representative procedure, as follows: 4,4-dimethyl-1,3-cyclohexanedione 7 (1 mole eq) (commercially available) and benzoyl cyanide are dissolved in anhydrous dichloromethane and cooled to 0° C. under an atmosphere of nitrogen. To the cooled solution is added anhydrous finely powdered zinc chloride (1.1 mole eq) followed by slow addition of triethylamine (1.2 mole eq). The reaction mixture is stirred at room temperature for 5-6 h and then poured into 2 M hydrochloric acid. The mixture is partitioned and the dichloromethane layer washed with 5% sodium carbonate. The aqueous carbonate phase is then acidified with hydrochloric acid and extracted with methylene chloride and dried (Na2SO4). The solvent is removed and the residue subjected to SiO2 column chromatography (hexane/ethyl acetate) affording 1-benzoyl-3,3,5-trimethylcyclohexan-2,6-dione 8. (W. J. Michaely and G. W. Kraatz, EP-B-135191).

Provenance & Evidence