Synthesize 4-Methoxyphenol from p-Anisaldehyde

4-Methoxyphenol is a kind of pink crystals or white waxy solid, also known as Mequinol which is   a drug used in combination with the drug tretinoin in the treatment of liver spots. It used alone and in higher doses is used as a topical drug for medical depigmentation. The Molecular Formula is C7H8O2, Molecular Weight is 124.14, EINECS is 205-769-8. 4-Methoxyphenol is stable, combustible, incompatible with halogens, oxidizing agents. The CAS Registry Number of 4-Methoxyphenol is 150-76-5. We should store it in a cool, dry place and store it in a tightly closed container.

It is the monomethyl ether of hydroquinone, and an isomer of guaiacol.It is often used to inhibit polymerization in monomers that polymerize with radical mechanisms, such as acrylates, methacrylates or styrene. In this article, I will show you how to synthesize 4-Methoxyphenol(CAS NO:150-76-5) from p-Anisaldehyde.

Firstly, in a 500 mL flask were placed 5.0 g (36.7 mmol) of p-anisaldehyde and 184 mL of methylene chloride (0.2M). This mixture was vigorously stirred with a magnetic stir bar. To the homogeneous solution was added 9.37 mL of 30% aqueous hydrogen peroxide (92.0 mmol., 2.5 equivalents) and 5.54 mL of formic acid (147 mmol., 4.0 equivalents). The flask was then fitted with a reflux condenser and heated to reflux for 20.5 hours with stirring.

After cooling, 119 mL of 1.5N sodium hydroxide (179 mmol., 4.86 equivalents) was added to the flask. The mixture was stirred for 15 minutes. The organic layer was separated and concentrated to a residue using a rotary evaporator. The residue was combined with the aqueous solution and 79.3 mL of methanol was added. The solution was stirred for 30 minutes. The methanol was removed using a rotary evaporator.

The neutral materials were removed from the aqueous residue by extracting with two 100 mL portions of methylene chloride. The solution was adjusted to a pH of 1 to 2 with concentrated hydrochloric acid. The 4-methoxyphenol was extracted with three 100 mL portions of methylene chloride.

The organic solution containing the neutrals as well as the one containing the product were separately dried over anhydrous magnesium sulfate and filtered into tared round-bottom flasks. The methylene chloride was removed using a rotary evaporator. A total of 0.052 g of neutrals was recovered. A total of 4.13 g of the crude 4-methoxyphenol was obtained.

The 4-methoxyphenol was purified utilizing bulb-to-bulb distillation. A mass of 3.88 g of 4-methoxyphenol as a white crystalline solid was obtained. The purity was determined by GC as well as HPLC.

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