Prop-2-enyl phenyl ether

The aromatic Claisen rearrangement involves the thermal transformation of a prop-2-enyl phenyl ether (1) into a 2-(prop-2-enyl)-cyclohexa-3,5-dienone... 

Conversion into 6-methyl-2-(4-methylphenyl)hepta- 1,5-diene. 2- 4-methyl-phenyl)prop-2-enyl vinyl ether. A mixture of the foregoing allylic alcohol (2.5 g), ethyl vinyl ether (75 ml) and freshly crystallised mercury(n) acetate (600 mg) is refluxed continuously for 12 hours on a water bath. The reaction mixture is chilled in ice and mixed with 10 per cent aqueous sodium carbonate solution (25 g) and stirred well for 30 minutes at 0 °C. The organic layer is... 

A protropic shift may be induced to effect double bond migration in the side chain by heating the allyl phenyl ether with methanolic potassium hydroxide when 2-(prop-l-enyl) phenol is formed (Expt 6.108). 

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