Sulfuric Acid → 3-Chloro-2,4-dimethylphenol

HRID 561914Notes

Reaction equation

HRID 561914 reaction equation
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])N.[OH:11]S(O)(=O)=O.NC(N)=O>O.[O-]S([O-])(=O)=O.[Cu+2]>[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([OH:11])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 1176UreaHCID 152786073-Chloro-2,4-dimethylaniline

Product 1

HCID 179117503-Chloro-2,4-dimethylphenol

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of 3-chloro-2,4-dimethyl-aniline (0.47 g, 3.0 mmol), in a mixture of water (3 mL) and conc. H2SO4 (2 ml), a solution of Na2NO2 (0.22 g) in H2O (5 ml) was added dropwise at 0° C. The mixture was stirred 1 h at 0° C., than treated with urea (0.2 g), stirred for 10 min at 0° C. A solution of CuSO4 (1.0 g) in water (6 mL) was added and the mixture was stirred for 60 h at RT. The reaction mixture was extracted with CH2Cl2 (2×20 ml), extracts were dried over Na2SO4 and evaporated. The residue was separated on SiO2 (4.0 g) column, hexane-EtOAc (0 to 10%). Brown crystals, 45 mg (0.29 mmol, 10%).

Workup

  1. stirringstirred for 10 min at 0° C
  2. stirringthe mixture was stirred for 60 h at RT
  3. extractionThe reaction mixture was extracted with CH2Cl2 (2×20 ml), extracts
  4. dry with materialwere dried over Na2SO4
  5. customevaporated
  6. customThe residue was separated on SiO2 (4.0 g) column, hexane-EtOAc (0 to 10%)

Sources & evidence

ORD record
ord-185995fff17c485f9e355f14d40354cc
Source dataset
uspto-grants-2011_11
Patent number
US08063225B2

Reaction notes

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