Nitric Acid → 3,4-Dimethyl-2-nitrophenol

HRID 1723010Notes

Reaction equation

HRID 1723010 reaction equation
[C:1]1([OH:9])[CH:6]=[CH:5][C:4]([CH3:7])=[C:3]([CH3:8])[CH:2]=1.[N+:10]([O-])([OH:12])=[O:11].C(OCC)(=O)C>C(O)(=O)C>[CH3:8][C:3]1[C:2]([N+:10]([O-:12])=[O:11])=[C:1]([OH:9])[CH:6]=[CH:5][C:4]=1[CH3:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 72493,4-DimethylphenolHCID 8857Ethyl Acetate

Product 1

HCID 135714543,4-Dimethyl-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 12.2 g of 3,4-xylenol in 100 ml of acetic acid was added a solution of 7.48 ml of 61% nitric acid in 50 ml of acetic acid while keeping the reaction temperature at 20° C. Then the mixture was reacted with stirring at room temperature for two hours. To the reaction mixture was added 200 ml of ethyl acetate and the mixture was washed successively with water, an aqueous solution of sodium hydrogencarbonate, water and a brine, and then, ethyl acetate was distilled away under reduced pressure. The residue was purified by subjecting to silica-gel column-chromatography [eluent:chloroform] to give 0.69 g of 3,4-dimethyl-2-nitrophenol.

Workup

  1. customat 20° C
  2. customThen the mixture was reacted
  3. washthe mixture was washed successively with water
  4. distillationan aqueous solution of sodium hydrogencarbonate, water and a brine, and then, ethyl acetate was distilled away under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-acb4c1764bac49ebb977100e93739c5d
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Reaction notes

Loading…