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 Synthesis of Pyrogallol 1-monomethyl ether
  • Synthesis of Pyrogallol 1-monomethyl ether
  • 1-monomethyl ether (CAS NO.: ), which is also known as pyrogallol monomethyl ether, could be produced through the following synthetic routes.

    Synthesis of Pyrogallol 1-monomethyl ether

    The apparatus consists of a 1-l. three-necked flask fitted with a gas inlet tube extending about 3 cm. into the flask and connected to the flask through a bubbler, a thermometer extending to the bottom, a mechanical stirrer, and a reflux condenser connected at the upper end with an exit tube leading to the hood. The reaction is carried out in an atmosphere of illuminating gas.

    In the flask are placed 60.8 g. (0.4 mole) of 2-hydroxy-3-methoxybenzaldehyde and 200 ml. of 2 N sodium hydroxide (0.4 mole). The mixture is stirred until almost all the solid has dissolved. The stirrer is replaced by a dropping funnel which contains 284 ml. (0.5 mole) of 6% hydrogen peroxide. With occasional shaking, the hydrogen peroxide is added in portions of 20–25 ml. About 1 hour is required for the addition; the temperature is kept between 40° and 50°. After the addition of the first portion of hydrogen peroxide, the temperature rises to about 45° and a dark solution results. The temperature is allowed to fall to 40° before the next portion of the peroxide is added.

    After all the hydrogen peroxide is added, the reaction mixture is allowed to cool to room temperature and is then saturated with sodium chloride, after which it is extracted four times with 100-ml. portions of ether. The combined extracts are dried over sodium sulfate. The ether is removed by distillation on a steam bath, and the residue is then distilled under reduced pressure. Pyrogallol monomethyl ether is collected at 136–138°/22 mm. The yield is 38–44.5 g. (68–80%) of a colorless to light yellow oil which solidifies on standing.


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