Sulfuric Acid → 3-Chloro-4-methoxyphenol

HRID 896455Notes

Reaction equation

HRID 896455 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])N.[OH:11]S(O)(=O)=O.N([O-])=O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 214413-Chloro-4-methoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 130819293-Chloro-4-methoxyphenolYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 0° C. solution of 3-chloro-4-methoxy aniline (1.0 g; 6.4 mmol) in 1:1 H2O: conc. H2SO4 (100 mL) was added very slowly a solution of NaNO2 (0.5 g; 7.6 mmol) in H2O (10 mL). Thick yellow fumes were emitted, and the black solution was then heated to reflux for 30 min. The mixture was extracted with EtOAc (4×50 mL) and the combined extracts were concentrated in vacuo. The residue was chromatographed (SiO2; 4:1 hex:EtOAc) to obtain 3-chloro-4-methoxy phenol (300 mg; 30%) as a yellow oil.

Workup

  1. temperaturethe black solution was then heated
  2. temperatureto reflux for 30 min
  3. extractionThe mixture was extracted with EtOAc (4×50 mL)
  4. concentrationthe combined extracts were concentrated in vacuo
  5. customThe residue was chromatographed (SiO2; 4:1 hex:EtOAc)

Sources & evidence

ORD record
ord-64707de86f3042599e721886cfe33e93
Source dataset
uspto-grants-2005_07
Patent number
US06919358B2

Reaction notes

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