2,3,4,5-Tetrahydro-1-benzoxepin-5-ol → 2,3-Dihydrobenzo[b]oxepine

HRID 1613607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1613607
O[CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:2]=[CH:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 2

HCID 3155762,3,4,5-Tetrahydro-1-benzoxepin-5-olHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 2567432,3-Dihydrobenzo[b]oxepineAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

800 ml of toluene are poured over 53 g (0.323 mole) of 5-hydroxy-2,3,4,5-tetrahydro-1-benzoxepin and, with addition of 3.7 g of p-toluenesulfonic acid monohydrate, the mixture is refluxed with a water trap for 1.5 hours. The cold organic phase is washed with saturated sodium bicarbonate solution, water and sodium chloride solution, and the solvent is evaporated off in vacuo. Kugelrohr distillation at 30°-35° C./0.008 torr results in 44 g of oil. p 1H NMR (60 MHz/CDCl3): δ=7.23-6.70 (m, 4H); δ=6.30 (m, 1H); δ=6.07-5.70 (m, 1H); δ=4.20 (t, J=5 Hz, 2H); δ=2.63 (m, 2H).

Aufarbeitung

  1. temperaturethe mixture is refluxed with a water trap for 1.5 hours
  2. washThe cold organic phase is washed with saturated sodium bicarbonate solution, water and sodium chloride solution
  3. customthe solvent is evaporated off in vacuo
  4. distillationKugelrohr distillation at 30°-35° C./0.008 torr

Quellen und Nachweise

ORD-Eintrag
ord-ce587cc7bc8b47cfb12635ddaa4c4cfe
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194442

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