In a dry 3-l. three-necked, round-bottomed flask fitted with an efficient reflux condenser, a stirrer, a Y-tube holding a 1-l. and a 250-ml. addition funnel, and protected from moisture by calcium chloride tubes is placed 5.76 g. (0.237 mole) of magnesium turnings barely covered by anhydrous ether. p-Bromotoluene (40 drops) and ethyl bromide (20 drops) are added, and the reaction starts immediately. p-Bromotoluene (35.0 g., 0.205 mole) in 200 ml. of anhydrous ether is added at such a rate that reflux is maintained. To the resultant solution of p-methylphenylmagnesium bromide is added, over a 1-hour period, a solution of 25.4 g. (0.200 mole) of dichloroacetone in 200 ml. of anhydrous ether.

At the same time, in a separate 2-l. three-necked, round-bottomed flask equipped with reflux condenser, stirrer, and addition funnel, ethylmagnesium bromide is prepared from 128.6 g. (1.18 moles) of ethyl bromide and 30 g. (1.23 moles) of magnesium in 800 ml. of anhydrous ether. When the reaction is complete, the addition funnel is replaced by a rubber stopper containing a short glass tube, and the reflux condenser is replaced by an exit tube lightly plugged with a small amount of glass wool. The Grignard reagent solution is forced, under mild nitrogen pressure, through the glass wool plug into the 1-l. addition funnel (Note 1). In the 250-ml. addition funnel is placed a filtered solution of 2.5 g. (0.0154 mole) of anhydrous ferric chloride in 200 ml. of anhydrous ether. Stirring is resumed, and the two solutions are simultaneously added to the dichloroacetone-p-methylphenylmagnesium bromide solution over a 2-hour period (Note 2). Stirring is continued for an additional 14 hours under dry nitrogen.

The reaction mixture is added to a slurry of 1500 g. of ice and 600 ml. of 2N hydrochloric acid saturated with ammonium chloride. The ether layer is separated, and the aqueous layer is extracted three times with 200-ml. portions of ether. The combined organic layers are washed with three 200-ml. portions of water until a neutral reaction is obtained with litmus and the wash water is free of chloride. The solution is dried over anhydrous magnesium sulfate and stored in a refrigerator. After evaporation of the ether, the residue is distilled at a low pressure through a short Vigreux column (Note 3). The fraction, b.p. 70–78° (0.4 mm.) (oil bath 100–135°), is collected to give 15–17 g. (51–57%) of the crude carbinol which crystallizes upon standing in an ice box. The product is recrystallized from pentane (4 g. per g. of alcohol) in an ice-salt mixture to give the pure alcohol, m.p. 38–39°.