Isopropyl phenyl ether

Isopropyl phenyl ether + excess hydrogen bromide + heat... 

The excess acidity method has been applied to the acid-catalysed hydrolysis of isopropyl phenyl ether at different temperatures.152... 

Boron trifluoride catalyzes the condensation of phenol and propylene to isopropyl phenyl ether and the subsequent rearrangement of this compound to o-isopropyl phenol. This rearrangement of an aryl alkyl ether is similar to the Fries reaction of phenolic esters (method 209). 

Capture of phenyl cations with methyl n-propyl ether gives products in which rearrangement has taken place.Initial capture gives the oxonium ion drawn to the left in equation 14. Most of this ion eliminates propene, and deprotonation of the resulting ion affords anisole (PhOR, where R = methyl), which constitutes 75% of the radiochemical yield. Among the other products are isopropyl phenyl ether (roughly 3% of the radiochemical yield, about 3 times more abundant than -propyl... 

To isopropyl phenyl ether and sodium iodide in dichloromethane/acetonitrile (1 1), silicon tetrachloride added and the mixture refluxed (14 h) to give phenol (acetals are also cleaved). 

Substituted isopropyl-protected guaiacols undergo transprotection in one step when treated with TMSOTf in anhydrous acetonitrile (eq 98) very high yields are obtained for this transformation if the substituent at position 6 is bulky and electron-withdrawing. However, mono- and disubstituted isopropyl phenyl ethers undergo Friedel-Crafts acetylation rather than transprotec-... 

Obtained by Friedel-Crafts acylation of isopropyl phenyl ether with homoveratroyl chloride in ethylene dichloride in the presence of aluminium chloride, first at 20°, then at 40° for 2-3 h and at r.t. overnight (31%) [5517]. 

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