Diethyl Ether → 1-[(2,2-Diethoxyethyl)thio]-3-methylbenzene

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Reaction Steps

In 90 mL of ethanol is dissolved 25 g of toluenethiol, to which are added 12.42 g of potassium hydroxide and 33.3 mL of bromoacetaldehyde diethyl acetal. The mixture thus obtained is heated under reflux for 2.5 hours. The reaction mixture is introduced into a mixture of ice water and diethyl ether, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is distilled under reduced pressure (113-125° C./2.5 mm Hg) to obtain 41.5 g of 1-[(2,2-diethoxyethyl)sulfanyl]-3-methylbenzene as an oily product.

Provenance & Evidence