EXPERIMENTAL PROCEDURES 27Preparation of 2-Allylphenol.The allyl ether is boiled in a flask undera reflux tube, the course of the rearrangement being conveniently fol-lowed by noting the refractive index at frequent intervals. When no hasrisen to 1.55 (five to six hours) the rearrangement is substantially com-plete with the minimum formation of undesirable by-products. Toseparate a small amount of 2-methyldihydrobenzofuran, the product isdissolved in twice its volume of 20% sodium hydroxide solution andextracted twice with petroleum ether (30-60°), from which the dihydro-benzofuran residue may be obtained by distillation. Ether should notbe used for this extraction as it removes some of the phenol from thealkaline 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 at103-105.5°/19 mm., nf> 1.5445, is obtained. 2-Allylphenol is a colorlessliquid, of guaiacol-like odor, with the following properties: b.p. 220°/
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