p-Toluenesulfonic acid → 2,3-Dihydro-7-nitro-1-benzoxepin

HRID 1613611Notes

Reaction equation

HRID 1613611 reaction equation
O[CH:2]1[C:8]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]2[O:6][CH2:5][CH2:4][CH:3]=[CH:2][C:8]=2[CH:9]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14580514HCID 14580514, compound

Product 1

HCID 145805152,3-Dihydro-7-nitro-1-benzoxepin

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

300 ml of toluene are poured over 25.1 g (0.12 mole) of 5-hydroxy-7-nitro-2,3,4,5-tetrahydro-1-benzoxepin and, with the addition of 1.5 g of p-toluenesulfonic acid, the mixture is refluxed with a water trap for 2 hours. The cold reaction solution is washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution, dried over sodium sulfate and filtered, and the solvent is evaporated off in vacuo. The residue is a solid of melting point 94°-95.5° C.

Workup

  1. temperaturethe mixture is refluxed with a water trap for 2 hours
  2. washThe cold reaction solution is washed with saturated sodium bicarbonate solution, water and saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated off in vacuo

Sources & evidence

ORD record
ord-8d8a62111e8b48b684dea9c1090f4c05
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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