Guaiacol → 2-Methoxy-6-nitrophenol

HRID 1089105Notes

Reaction equation

HRID 1089105 reaction equation
O.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[N+:11]([O-])([OH:13])=[O:12]>CCOCC>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[OH:10]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 944Nitric AcidHCID 962Water

Product 1

HCID 109428552-Methoxy-6-nitrophenol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 50 ml of water, 150 ml of ether and 15.0 g of 2-methoxyphenol was added dropwise 12.7 ml of 61% nitric acid, and the mixture was stirred at room temperature for 15 minutes. The ether layer was separated from the aqueous layer and dried over anhydrous sodium sulfate. After the drying agent was filtered off, the solvent was distilled off under reduced pressure. The residue was purified by silica-gel column-chromatography using Wakogel® C-200 [eluent: chloroform-n-hexane (1:1)] to give 4.72 g of 2-methoxy-6-nitrophenol.

Workup

  1. customThe ether layer was separated from the aqueous layer
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationAfter the drying agent was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica-gel column-chromatography

Sources & evidence

ORD record
ord-6d536cd4bff94a76b2ef5ad4258f815a
Source dataset
uspto-grants-1990_10
Patent number
US04965261

Reaction notes

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