p-Toluenesulfonic acid → 2-Nitro-6-(tetrahydropyran-2-yloxy)phenol

HRID 1105811Notes

Reaction equation

HRID 1105811 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.[OH:18][C:19]1[C:24]([OH:25])=[CH:23][CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27]>C1C=CC=CC=1>[OH:18][C:19]1[C:24]([O:25][CH:17]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:23][CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 4675622Nitrocatechol

Product 1

HCID 129015162-Nitro-6-(tetrahydropyran-2-yloxy)phenol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.030 g of p-toluenesulphonic acid and 17.8 g of 3,4-dihydro-2H-pyrane are added to a mixture of 29.8 g of 2,3-dihydroxy-nitrobenzene in 400 ml of absolute benzene and the solution is left to stand for 7 days at 20°. It is filtered through 15 g of a silica gel formulation (Merck silica gel 60; grain size 0.063-0.200 mm) and the silica gel is rinsed with benzene. After distilling off the benzene under reduced pressure, a reddish oil is obtained which, when crystallised from hexane, gives 2-hydroxy-3-(tetrahydropyran2-yloxy)-nitrobenzene in the form of yellow crystals; melting point 72°-73°.

Workup

  1. waitthe solution is left
  2. filtrationIt is filtered through 15 g of a silica gel formulation (Merck silica gel 60; grain size 0.063-0.200 mm)
  3. washthe silica gel is rinsed with benzene
  4. distillationAfter distilling off the benzene under reduced pressure
  5. customa reddish oil is obtained which, when
  6. customcrystallised from hexane

Sources & evidence

ORD record
ord-92ebb37cbf8b46798950082e04b78a30
Source dataset
uspto-grants-1982_01
Patent number
US04310527

Reaction notes

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