Triethyl carbinol (CAS NO.: ), which is also known as 3-ethyl-3-pentanol, could be produced through the following synthetic routes.

In a 3-l. three-necked flask, fitted with a mechanical stirrer, a 500-cc. separatory funnel, and an efficient reflux condenser to which a calcium chloride tube is attached, are placed 107 g. (4.4 gram atoms) of magnesium turnings and 800 cc. of anhydrous ether. The reaction is started by adding 5 cc. (7 g., 0.06 mole) of ethyl bromide without stirring. The stirrer is started, and a solution of 480 g. (4.4 moles) of ethyl bromide in 1 l. of anhydrous ether is added as rapidly as the refluxing of the ether allows. The addition requires about two hours. The reaction is practically complete when all the halide has been added, but stirring should be continued for fifteen minutes longer.

A solution of 156 g. (1.32 moles) of ethyl carbonate in 200 cc. of ether is added to the Grignard reagent, with rapid stirring, over a period of approximately three hours. The reaction is vigorous, and the ether refluxes continually. After all the diethyl carbonate has been added, the flask is heated on a water bath and stirring is continued for another hour.

The reaction mixture is hydrolyzed by pouring it, with frequent shaking, into a 5-l. round-bottomed flask containing 1.5 kg. of cracked ice and a solution of 300 g. of ammonium chloride in 600 cc. of water. The ether layer is separated in a large separatory funnel, and the aqueous residue is extracted with two 500-cc. portions of ether.

The ether is distilled from the combined extracts, and the crude triethyl carbinol is dried with 10 g. of anhydrous potassium carbonate. The alcohol is then distilled at atmospheric pressure, and the portion (80–90 g.) boiling at 139–142° is collected. The low-boiling distillate is treated with 5 g. of anhydrous potassium carbonate, filtered, and redistilled, whereby another portion (about 25 g.) of triethyl carbinol boiling at 139–142° is obtained. The process is repeated once, or twice if necessary, and an additional 20 g. is collected. The total yield is 125–135 g. (82–88 per cent of the theoretical amount). Triethyl carbinol is a viscous liquid with a penetrating, camphor-like odor.