Ethylene Glycol → 8-Phenyl-1,4-dioxaspiro[4.5]decane-8-carbonitrile

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Reaction Steps

4-cyano-4-phenylcyclohexanone (5.97 g, 30 mmole) was taken up in toluene (200 ml) and ethylene glycol (4 ml, 71.6 mmole) was added. After addition of p-toluenesulfonic acid (86 mg, 0.5 mmole) the reaction mixture was heated to the boil in a water separator. The course of the reaction was followed by thin layer chromatography. After 20 hours no starting product could be detected any longer by thin layer chromatography. After cooling, the toluene solution was extracted by shaking with water (5×30 ml) and saturated aqueous NaCl solution (3×20 ml) and dried over Na2SO4. After removing the solvent on a rotary evaporator the desired ketal was obtained in a yield of 6.8 g (94%) as a white solid with a melting point of 108°-110° C.

Provenance & Evidence