5-Methoxy-o-toluidine → 5-Methoxy-2-methylphenol

HRID 1505308Notes

Reaction equation

HRID 1505308 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:3]=1N.N([O-])=[O:12].[Na+]>OS(O)(=O)=O>[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:3]=1[OH:12]

Participants

4

Reactant 2

HCID 995005-Methoxy-o-toluidine2×HCID 23668193Sodium Nitrite

Product 1

HCID 109535825-Methoxy-2-methylphenol

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-methyl-5-(methyloxy)aniline (Intermediate 11, 6.0 g) in H2SO4 (5 M, 20 mL) was added portionwise NaNO2 (3.4 g, 49.3 mmol) at 0-5° C. The mixture was stirred at 50° C. for 1 hour and extracted with ethyl acetate (4 times 30 mL). The combined ethyl acetate layers were dried over sodium sulphate and concentrated under vacuum to give a residue, which was purified by column chromatography on silica gel (with EtOAc:PE=1:20 as eluents) to afford the title compound as a solid.

Workup

  1. extractionextracted with ethyl acetate (4 times 30 mL)
  2. dry with materialThe combined ethyl acetate layers were dried over sodium sulphate
  3. concentrationconcentrated under vacuum
  4. customto give a residue, which
  5. customwas purified by column chromatography on silica gel (with EtOAc:PE=1:20 as eluents)

Sources & evidence

ORD record
ord-16ffb470dad84de7954b70e1566697e7
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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