Hydrochloric Acid → HCID 178458818, compound

Participants

Reaction Steps

A mixture of 3-hydroxy-5-(5-indanyl)cyclohex-2-en-1-one (5.0 g; 22 mmole) in dichloromethane (100 ml) and pyridine (1.74 g; 22 mmole) was stirred at room temperature whilst propionyl chloride (1.92 g; 22 mmole) was added dropwise over a period of two minutes. Stirring was continued for 1 hour after which the organic solution was washed with water (2×100 ml), dried over anhydrous sodium sulphate, and the solvent was removed under reduced pressure using a rotary evaporator. The resulting brown oil was immediately dissolved in 1,2-dichloroethane (50 ml) and added dropwise to a mixture of aluminium trichloride (5.85 g; 44 mmole) in 1,2-dichloroethane (50 ml) over 30 min at such a rate that the temperature did not exceed 30° C. After stirring for 30 min at room temperature, the solution was poured into 100 ml of a 1:1 mixture of concentrated hydrochloric acid and water. The organic solution was washed with water (2×200 ml), dried over anhydrous sodium sulphate and the solvent was removed moved under reduced pressure using a rotary evaporator. The resulting yellow oil was purified by chromatography over silica gel (eluant dichloromethane) to give 3-hydroxy-5-(5-indanyl)-2-propionylcyclohex-2-en-1-one, (1.71 g; 27%) as a yellow solid, mp 98° C.

Provenance & Evidence