Chloromethyl Methyl Ether → 3-Methoxymethyloxyphthalic anhydride

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Reaction Steps

N,N-Diisopropylethylamine (4.39 g, 34.0 mmol) was added to a solution of 3-hydroxyphthalic anhydride (5.0 g, 30.5 mmol) in dichloroethane (60 ml), then chloromethyl methyl ether (2.57 g, 32.0 mmol) was dropped thereinto under cooling with ice water and the mixture was returned to room temperature and stirred for 1 hour. Then N,N-diisopropylethylamine (2.20 g, 17.0 mmol) and chloromethyl methyl ether (1.28 g, 16.0 mmol) were further added thereto followed by stirring for 1 hour. After the reaction, the solvent was evaporated and the residue was diluted with water followed by extracting with ether. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom to provide 6.3 g (yield 99%) of 3-methoxymethyloxyphthalic anhydride as colorless oil.

Provenance & Evidence