Abstract
Catechol dimethyl ether (1) was made from ο-anisidine by a method similar to that described in a previous paper.
Also resorcinol dimethyl ether (2) was made from m-anisidine. The effects of kinds of acids, catalysts, illumination with UV light, concentration of acid and reaction temperature on diazotization and decomposition of the diazonium compound in methanol were examined.
Sulfuric acid was preferred for the diazotization and the decomposition. No catalysts were effective.
Under illumination with UV light, decomposition time of the diazonium compounds was shortened. Decomposition of ο-anisolediazonium compound without UV light led exclusively to production of anisole (yield 60.4 mole%).
With UV light, the products were anisole (19.7 mole%), (1) (24.7 mole%) and catechol monomethyl ether (5.3 mole%).
On the other hand, (2) was obtained in the maximum yield (64.7 mole%) under the following conditions ; reaction temperature 65°C, pH= 1, without catalyst and with UV light.
