As the result of a large number of methylations carried out with phenol with dimethyl sulfate as the methylating agent, the following conclusions have been drawn: 1. Anisol is not methylated by the action of methyl sulfate on an aqueous solution of phenol in either neutral or acid condition. 2.The presence of either sodium or potassium hydroxide results in the methylation of phenol. 3.The amount of methylation is in the same order as the ratio of alkali to phenol, a tenth mol of alkali resulting in about a 10% methylation. An excess of alkali has no influence, at least in the direction of greater action. 4.The second methyl group can be used in methylation to a considerable extent; this is based upon the use of a half mol of dimethyl sulfate and one mol of phenol, in the presence of two to four mols of water and a mol and a half of sodium hydroxide, where yields as high as 70% of anisol have been obtained. 5.Considerable methylation takes place even at low temperatures with the first group entering into the reaction. Practically all of the first group may be used in this way. 6. Other things being equal, an increase in the amount of water present causes a decrease in the amount of methylation, two mols of water to one mol of phenol and one and a half mols of sodium hydroxide being about the lowest practical amount which can be used.
Proceedings of the Iowa Academy of Science
©1924 Iowa Academy of Science, Inc.
Lewis, Harry F. and Trieschmann, Wesley
"Conclusions in Regard to the Methylation of Phenol,"
Proceedings of the Iowa Academy of Science, 31(1), 282-282.
Available at: https://scholarworks.uni.edu/pias/vol31/iss1/69