2624-43-3

White Solid

Ondogyne,Roussel,France,1970

Cyclofenil is a weak nonsteroidal estrogen with ovulation induction properties.

Cyclofenil is a weak nonsteroidal estrogen with ovulation induction properties. Mammalian hormone.

ChEBI: Cyclofenil is an organic molecular entity.

(A) Preparation of p-Hydroxy-p'-Methoxybenzhydrylidenecyclohexane: To a Grignard solution prepared from 110 g of magnesium (4.5 mols) and 840 g of p-bromoanisole (4.5 mols) in one liter of anhydrous ether, there was added dropwise with vigorous agitation 307 g of p-hydroxyphenyl cyclohexyl ketone (1.5 mols) dissolved in one liter of anhydrous ether. Upon completion of the addition the reaction mixture was refluxed for 2.5 hours with agitation, and was then cooled. Thereupon 15 mols of ammonium chloride dissolved in 3 liters of water were added. The ethereal layer was separated, washed with water, dried over anhydrous sodium sulfate and distilled. Yield: 370 g. BP 180° to 190°C at 0.1 mm. The substance was recrystallized from a mixture of carbon tetrachloride and petroleum ether. MP 145° to 146°C.
(B)Preparation of p,p'-Dihydroxybenzhydrylidenecyclohexane: A mixture of 118 g of p-hydroxy-p'-methoxybenzhydrylidenecyclohexane (0.4 mol), 120 g of potassium hydroxide pellets and 500 ml of triethylene glycol was stirred 4 hours at 220°C. When the reaction mixture was poured into water the substance crystallized, and the crystals were filtered off and washed with water. The substance was then recrystallized from a mixture of ethanol and petroleum ether. Yield: 104 g. MP 235° to 236°C.
(C) Preparation of p,p'-Diacetoxybenzhydrylidenecyclohexane: 56 g of p,p'- dihydroxybenzhydrylidenecyclohexane (0.2 mol) was mixed with 250 ml of acetic anhydride and 500 ml of pyridine. The mixture was refluxed for 2 hours and was then poured into water, the substance crystallizing out. The crystals were filtered off and washed with water. Finally the substance was recrystallized from ethanol. Yield: 62 g. MP 135° to 136°C.

Ovulation stimulant