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2-methyl-2-phenyltetrahydrofuran
2-methyl-2-phenyltetrahydrofuran Basic information
- Product Name:
- 2-methyl-2-phenyltetrahydrofuran
- Synonyms:
-
- Furan, tetrahydro-2-methyl-2-phenyl-
- 2-Methyl-2-phenyltetrahydrofuran
- CAS:
- 21865-78-1
- MF:
- C11H14O
- MW:
- 162.23
- Mol File:
- 21865-78-1.mol
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2-methyl-2-phenyltetrahydrofuran Chemical Properties
- Boiling point:
- 105-106 °C(Press: 20 Torr)
- Density
- 1.014 g/cm3(Temp: 26 °C)
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2-methyl-2-phenyltetrahydrofuran Usage And Synthesis
Synthesis
The synthesis of 2-methyl-2-phenyltetrahydrofuran is typically achieved through the cyclization of a suitable linear precursor (usually a 1,4-diol or a related functionalized ether). One efficient method is the acid-catalyzed cyclization of 4-phenyl-4-penten-1-ol or a derivative thereof. The double bond in the pentenol is protonated by a strong acid (e.g., H₂SO₄ or TsOH) to generate a carbocation intermediate, which is then attacked by the hydroxyl group to form a five-membered tetrahydrofuran ring. Alternatively, the compound can also be prepared via a Grignard reaction of 4-hydroxybutyrate with phenylmagnesium bromide, followed by reduction and subsequent acid-catalyzed cyclization.