4,4,5,5-Tetramethyl-l,2-dioxolan-3-one

In a dry and argon-flushed flask, 4,4,5,5-tetramethyl-l,3-dioxolane-2-one 0-phenylsulfoxime (199 593 mg, 1.98 mmol) is dissolved in CH2CI2 (15 mL). 2-Methoxyphenylmagnesium bromide (solution in diethyl ether, 2.2 mmol) is added and the reaction mixture is stirred 30 min at 25 °C. The reaction mixture is cooled to 0 °C and quenched with pH 9 buffer. Standard workup gives the crude imine, which is dissolved in methanol (10 mL) and cooled to 0 °C. HCI (4 mL, 1 M in diethyl ether) is added and the mixture stirred 1.5 h at 25 °C. Volatile materials are removed in vacuo and dry diethyl ether (40 mL) is added. Filtration gives 2-methoxyaniline hydrochloride (200 305 mg, 96%) as a pale purple powder. ... 

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