Help with the workup of 4-methoxyanisole
Hello,
Recently I attempted to prepare the dimethyl ether of hydroquinone, or 1-4 dimethoxybenzene, using methyl tosylate with KOH as the base in aqueous
solution.
The product has an interesting odor- soapy, anise-like and pretty persistent.
However, I received a yield a bit over 200% (32g), with some appearing as flakes, the rest as a few hard crystal rocks. This does not appear to be
possible if the product is pure.
My first idea was the excess weight was due to potassium tosylate, which would have reduced solubility in the reaction mixture, with all the dissolved
potassium salts.
To this end, I stirred the product in boiling water. Some dissolved, but about ~125% of the anticipated yield of methoxyanisole did not dissolve and
instead was molten at ~80C (this was separated by decanting, and the molten material formed the rocklike solid,) the remaining solution on cooling is
currently forming plate-like crystals.
Anyone have experience with this reaction? What could be the identities of the seeming 2 different materials?
My best guess for recrystallization is a binary alcohol-water system, but what is the impurity? (A phenol-tosyl ester?)
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