Sodium Iodide → Methyl 4-(benzyloxy)-3,5-dimethoxybenzoate

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Reaction Steps

A mixture of 21.2 g. of methyl syringate, 15 g. of potassium carbonate, 1 g. of sodium iodide, 70 ml. of 95% ethanol (5% methanol), and 14 g. of benzyl chloride was heated at reflux with stirring for 4 hours. The alcohol was stripped off, ice water added, and the mixture extracted with ether. The ether exxtract was washed with water and the ether stripped off. Benzene was added and stripped to remove traces of water. The residual oil was dissolved in isopropanol, charcoal added, and the mixture filtered. Hexane was added and the solution cooled. A total of 19 g. (63% yield) of methyl 3,5-dimethoxy-4-benzyloxybenzoate, m.p. 62°-65° C., was obtained.

Provenance & Evidence