Epichlorohydrin → 2-[(2-Tert-butyl-4-methoxyphenoxy)methyl]oxirane

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Reaction Steps

In 150 ml of methyl ethyl ketone were dissolved 4.5 g (0.025 mole) of 4-hydroxy-3-tert-butylanisole and 8 g of epichlorohydrin, and 7.0 g of potassium carbonate is added to the resultant solution, followed by heating under reflux for 8 hours. The precipitated inorganic salt is filtered out, and the filtrate is concentrated. The oily-formed residue is extracted with ethyl acetate, and the extract is washed successively with 1% aqueous sodium hydroxide and water, and the ethyl acetate is distilled off to give about 5 g of 4-(2,3-epoxypropoxy)-3-tert-butylanisole in the form of oily substance. The oily substance and 4.6 g of tert-butylamine are dissolved in 100 ml of methanol, followed by heating under reflux for 10 hours, and the solvent is distilled off. The oily residue is admixed with 200 ml of water, and the mixture is made acid with hydrochloric acid, stirred and extracted with isopropyl ether to remove the unreacted materials. The resulting aqueous solution is concentrated under reduced pressure, and the white crystals that crystallize out are recovered by filtration. Recrystallization from water gives 1.3 g of the objective compound, m.p. of 177° to 179° C.

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