2-Formyl-6-«-butyl-6-methylcyclohexanone

A higher-boiling fraction consisting of 2-formyl-6- -butyl-6-methylcyclohexanone, b.p. 201-203° (20 mm.), is obtained if hydrolysis is not complete. 

In a 1-1. three-necked flask equipped with a dry ice-acctone condenser and a sealed mechanical stirrer is placed 700 ml. of commercial, anhydrous, liquid ammonia. To the stirred ammonia is added a small piece of potassium metal. (Caution1 Care should he exercised in handling potassium metal, since it is extremely reactive and it ignites on contact with water, atmospheric moisture, or alcohol. It should he manipulated under toluene or xylene, and blotted with filter paper before addition.) After the appearance of a blue color a few crystals of ferric nitrate hydrate (ca. 0.1 g.) are added, followed by small pieces of freshly cut potassium metal until 7.0 g. (0.18 g. atom) has been added. After all the potassium has been converted to the amide (Note 7), 24.9 g. (0.154 mole) of sodio-2-formyl-6-methylcyclohexanone is added carefully through a powder funnel (Note 8). After 1 hour a solution of 28.2 g. (0.21 mole) of w-butyl bromide (Note 9) in 50 ml. of anhydrous ether is added dropwise from an addition funnel. The mixture is stirred for 3 hours, and then the dry ice-acetone condenser is replaced by a water condenser. A steam bath is placed under the flask, and the ammonia is evaporated (Caution ) as 400 ml. of anhydrous ether is added. When the... 

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