Water → 4-(1-Hydroxy-2-methylpropan-2-yl)benzonitrile

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Reaction Steps

p-(1,1-Dimethyl-2-hydroxyethyl)bromobenzene, 148 g, 0.646 mole, was added to a 1 L flask fitted with a reflux condenser, magnetic stirrer and oil bath. Dimethylformamide, 350 mL, and cuprous cyanide, 69.4 g, 0.775 mole were then added to the flask. The heterogeneous mixture was heated to gentle reflux whereupon it became somewhat more homogeneous and would then easily stir. The mixture was heated at reflux for five hours. While still hot the mixture was cast into 1 L of water using 100 mL of hot DMF for washing out the flask. The precipitated residue was stirred by hand as well as possible, allowed to settle and the greater portion of the water decanted and discarded. A freshly prepared solution of ferric chloride, 340 g; conc. HCl, 85 mL; water, 510 mL was added to the residue to destroy copper complexes. The mixture was heated with good stirring at 60° to 70° C. for 20 to 30 minutes. The crude nitrile was then extracted with three 200 mL portions of benzene. The benzene extracts were combined and dried over anhydrous K2CO3 for 1/2 hour. Benzene was removed in a rotoevaporator to give a yellowish oil which crystallized easily when cooled to room temperature and scratched. The yield was about 102 g (90%), mp=70°-82° C.

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