Group of substances:

Empirical formula (Hill's system for organic substances):

Structural formula as text:

Molar/atomic mass: 134.175

Melting point (°C):

Boiling point (°C):

Solubility (g/100 g of solvent):

Density:

Synthesis 1:

The phenyl allyl ether is boiled in a flask under a reflux tube, the course of the rearrangement being conveniently followed by noting the refractive index at frequent intervals. When no has risen to 1.55 (five to six hours) the rearrangement is substantially complete 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 dihydrobenzofuran 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 extracted with ether; the extract is dried over calcium chloride and distilled under diminished pressure.

A 73% yield of material boiling at 103-105.5°/19 mm., nD = 1,5445, is obtained. 2-Allylphenol is a colorless liquid, of guaiacol-like odor, with the following properties: b.p. 220°/760 mm., 99°/12 mm., nD = 1,5453.

Reactions of synthesis:

1. Yeild 73%. [Ref.1, Ref.2]
   C₆H₅OCH₂CH=CH₂ → C₆H₄(OH)CH₂CH=CH₂
   

Reactions:

1. Yeild 75%. [Ref.1]
   C₆H₄(OH)CH₂CH=CH₂ → C₆H₄(OH)CH=CHCH₃
   

References:

1. CRC Handbook of Chemistry and Physics. - 90ed. - CRC Press, 2010. - pp. 3-12
   
2. Lewis R.J. Sax's Dangerous Properties of Industrial Materials. - 11ed. - Wiley-interscience, 2004. - pp. 124
   
3. Свойства органических соединений: Справочник. - Под ред. Потехина А.А. - Л.: Химия, 1984. - pp. 374-375 [Russian]
   
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   © Collected Ruslan Anatolievich Kiper, burewestnik@mail.ru