- Production Method of tert-Butyl p-toluate
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tert-Butyl p-toluate (CAS NO.: ), which is also known as , 4-methyl-, 1,1-dimethylethyl ester, could be produced through the following synthetic routes.
A 200-ml., one-necked, round-bottomed flask equipped with a Claisen adapter, a condenser, an addition funnel, and a magnetic stirring bar is charged with 50 ml. of tert-butyl alcohol. Under nitrogen, 22.6 ml. of a 1.55 M solution (0.0350 mole) of n-butyllithium in hexane is added slowly from a syringe, giving a turbid reaction mixture. A water bath is used to keep the mixture near room temperature. After stirring for 15 minutes, a solution of 5.42 g. (0.0351 mole) of p-toluoyl chloride in 25 ml. of anhydrous diethyl ether is added dropwise to the stirred mixture. The resulting yellow slurry is stirred at room temperature for 15 hours. The yellow suspension is transferred with 100 ml. of ether to a separatory funnel and washed with three 25-ml. portions of saturated sodium chloride, and dried over magnesium sulfate. The ether is removed by distillation, and the residual oil distilled under reduced pressure, yielding a small forerun (0.10 g.) and 5.31–5.51 g. (79–82%) of tert-butyl p-toluate, b.p. 98–101° (4.2 mm.).
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