3,4-dihydro-2H-pyran → 2-Nitro-6-(tetrahydropyran-2-yloxy)phenol

HRID 636508Notes

Reaction equation

HRID 636508 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[OH:11])([O-:3])=[O:2].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)[C:5]=1[OH:11])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 4675622Nitrocatechol

Product 1

HCID 129015162-Nitro-6-(tetrahydropyran-2-yloxy)phenolYield 54.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 3-nitrobenzene-1,2-diol (2.78 g) and 3,4-dihydro-2H-pyrane (1.81 g) in benzene (39 ml) was added p-toluenesulfonic acid monohydrate (5 mg) at ambient temperature, and the mixture was stirred for 24 hours. The reaction mixture was washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform—methanol) and crystallized with n-hexane to give 2-nitro-6-(tetrahydropyran-2-yloxy)phenol (2.32 g).

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (chloroform—methanol)
  5. customcrystallized with n-hexane

Sources & evidence

ORD record
ord-f6d850c330424f4b8ebb67f24f0f998a
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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