Sodium Hydroxide → 1-Methyl-4-oxocyclohexane-1-carbonitrile

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Reaction Conditions

Reaction Steps

8-methyl-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (3.29 g, 18.1 mmol) was dissolved in a 1:1 mixture of THF and 3N HCl aqueous solution (60 mL). The resulting mixture was stirred at 40° C. for 5 h, cooled to 0° C. and neutralized using about 30 mL of a 3N NaOH aqueous solution until a basic pH was reached. It was extracted with ether (4×75 mL). The organic portions were combined, dried over anhydrous Na2SO4 and concentrated. The crude was purified by silica gel column chromatography using a gradient from 15% EtOAc:hexanes to 20% EtOAc:hexanes as eluent to afford 1-Methyl-4-oxo-cyclohexanecarbonitrile as a white solid (1.82 g, 73%).

Provenance & Evidence