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Organic Lab Reactions 32 - EXPERIMENTAL PROCEDURES 27...

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EXPERIMENTAL PROCEDURES 27 Preparation of 2-Allylphenol. The allyl ether is boiled in a flask under a reflux tube, the course of the rearrangement being conveniently fol- lowed by noting the refractive index at frequent intervals. When no has risen to 1.55 (five to six hours) the rearrangement is substantially com- plete with the minimum formation of undesirable by-products. To separate a small amount of 2-methyldihydrobenzofuran, the product is dissolved in twice its volume of 20% sodium hydroxide solution and extracted twice with petroleum ether (30-60°), from which the dihydro- benzofuran residue may be obtained by distillation. Ether should not be used for this extraction as it removes some of the phenol from the alkaline solution. The alkaline solution is acidified and the phenol ex- tracted with ether; the extract is dried over calcium chloride and dis- tilled under diminished pressure. A 73% yield of material boiling at 103-105.5°/19 mm., nf> 1.5445, is obtained. 2-Allylphenol is a colorless liquid, of guaiacol-like odor, with the following properties: b.p. 220°/
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