The hydrolysis of ether bonds is a potentially green method for using plants as a source of chemicals. Although the arylalkyl ether anisole can be hydrolyzed to phenol and methanol in the presence of aluminum chloride, the method has the disadvantage that it produces large amounts of alumina as by product. Since the carbon atoms of ethers that are directly bound to the oxygen have carbonium ion character, nucleophilic attack is a possible route to inducing cleavage of these carbon-oxygen bonds. The hydrolysis of the carbon-oxygen bond in ethers is induced by molybdate as nucleophile, or by aluminum phosphate in combination with ultrasound. High yields are obtained with epoxides, and significantly lower yields with trimethylene oxide and tetrahydrofuran. The molybdate or phosphate oxoanion acts as the nucleophile. Calculations have been carried out to determine patterns affecting the enthalpy of the hydrolysis of ethers to alcohols. These show that the reaction is close to being thermoneutral, but that both ether hydrolysis and ether ammonolysis are enthalpically favored, especially for ethers that have sterically bulky or fluorinated substituents. (C) 2002 Elsevier Science B.V. All rights reserved.