2,3,4,5-Tetrahydro-1-benzoxepin-5-ol → 2,3-dihydro-1-benzoxepine

HRID 1613607Notes

Reaction equation

HRID 1613607 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 2567432,3-dihydro-1-benzoxepineYield 93.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ce587cc7bc8b47cfb12635ddaa4c4cfe
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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