Benzene → Methyl 2-methyl-5-nitrobenzyl ether

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Reaction Steps

2-Methyl-5-nitrobenzyl chloride (10.2 g) is dissolved in methanol (180 ml). Sodium methoxide (5.4 g) is added and the mixture is refluxed. The reaction is monitored by thin layer chromatography (75:25, hexane:benzene). Additional quantities of sodium methoxide are added and heating continues until the reaction is complete. The reaction mixture is then cooled and filtered. The filtrate is concentrated under vacuum. The residue is dissolved in methylene chloride, washed with water, and the organic layer is then dried over magnesium sulfate. Removal of the drying agent by filtration and concentration of the filtrate under vacuum leaves 15.8 g of solid material which when recrystallized from hexane (150 ml) yields 11.5 g of product as a white solid having a melting point from 45° to 52° C.

Provenance & Evidence