Sodium hydroxide with chloroethane

A mixture of 10.0 g of 3-methylsulfinyl phenothiazine (MP 193° to 195°C), 6.1 g of finely powdered sodium hydroxide and 125 cc of toluene is boiled for 1 hour under reflux with a water separator on an oil bath kept at a temperature of 150°C, while the mixture is stirred. Without interrupting the boil a solution of 7.0 g of 2-(N-methvl-piperidyl-2 )-1-chloroethane (BP 84°C/10 mm Hg) in 10 cc of toluene is added dropwise in the course of 1 hour, after which boiling is continued for another 3 hours. When the reaction mixture has cooled it is first washed with 25 cc of water three times and then extracted with 75 cc of a 15% aqueous tartaric acid solution. The tartaric acid extract is shaken out with 25 cc... 

A solution of 52.5 ml l-dimethylamino-2-chloroethane in 200 ml toluene is added at a temperature below 20°C the mixture is refluxed for 20 h and cooled, and 100 ml t-butanol are added. The mixture is agitated for 1 h at room temperature, 35 ml ethanol are added, and the mixture is again agitated for 30 min at room temperature. It is then extracted with 2 N hydrochloric acid the acidic phases are washed with ether, made alkaline by the addition of sodium hydroxide solution, and extracted with ether the ethereal phases are washed with water, dried over magnesium sulphate and then distilled to dryness under a vacuum. The residue is dissolved in 100 ml methanol 300 ml of a saturated solution of fumaric acid in methanol are added the methanol is distilled off and replaced by ethyl acetate. Crystallization is allowed to commence and the mixture is cooled with ice for 30 min and suction-filtered the precipitate is washed with water and dried. 

SAFETY PROFILE An intense irritant to dssue, skin, and eyes. Flammable by chemical reaction. Ignites or explodes with heat or grinding. Explosive reaction with moisture, chromium trioxide, potassium chlorate, halocarbons (e.g., l,l-diethoxy-2-chloroethane), oxidants, sodium nitrite, air. Can become explosive in storage. Violent reaction with dinitrogen tetraoxide. Will react with water or steam to produce heat and toxic and corrosive fumes of sodium hydroxide and ammonia. When heated to decomposition it emits highly toxic fumes of NH3 and Na20. See also AMIDES. 

In Reaction 1.1, you saw that chloroethane reacts with sodium hydroxide to give ethanol, which is a primary alcohol, and sodium chloride. Imagine that you needed to prepare not a primary alcohol, but the tertiary alcohol, 2-methylpropan-2-ol (Structure 2.1) and that you had 2-chloro-2-methylpropane (Structure 2.2) available. You might try to prepare the alcohol from the chloride (Structure 2.2) using aqueous sodium hydroxide. In fact, as seen in Reaction 2.1, the product of this reaction is not the desired alcohol (Structure 2.1) but the alkene (Structure 2.3)... 

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