Water → 3-Methoxy-2-methylphenol

HRID 1505347Notes

Reaction equation

HRID 1505347 reaction equation
[CH3:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:3]=1N.N([O-])=[O:12].[Na+].O>OS(O)(=O)=O>[CH3:1][C:2]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:3]=1[OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 118048223-Methoxy-2-methylaniline2×HCID 23668193Sodium Nitrite

Product 1

HCID 2489133-Methoxy-2-methylphenolYield 43.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-methyl-3-(methyloxy)aniline (Intermediate 58, 1.31 g) in H2SO4 (6 M, 100 mL) was added portionwise NaNO2 (794 mg, 11 mmol) at 0° C. The mixture was stirred for another 2 hours at 40° C. and water (100 mL) was added. The resulting mixture was extracted with ethyl acetate (3 times 100 mL) and the combined ethyl acetate phases were dried and evaporated. The residue was purified by silica gel column chromatography (PE:EtOAc=5:1) to afford the title compound as a solid (569 mg).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (3 times 100 mL)
  2. dry with materialthe combined ethyl acetate phases were dried
  3. customevaporated
  4. customThe residue was purified by silica gel column chromatography (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-f68014328439473fb5fbe1c54361f94f
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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