Nitric Acid → HCID 14345188, compound

HRID 1824704Notes

Reaction equation

HRID 1824704 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[C:5]([OH:8])=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=1

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 280504-Chloroguaiacol

Product 1

HCID 14345188HCID 14345188, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-2-methoxyphenol (1.77 g) was dissolved in acetic acid (18 mL). To this solution, a separately prepared nitric acid solution (mixture of 70% nitric acid (1.88 mL) and acetic acid (5 mL)) was added under ice cooling with stirring. The mixture was stirred at room temperature for 1 hour, diluted with ethyl acetate, and washed with water. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain a crude product. This product was purified by silica gel chromatography (ethyl acetate:n-hexane=4:1 v/v) to obtain the title compound (1.8 g).

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. washwashed with water
  3. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customto obtain a crude product
  6. customThis product was purified by silica gel chromatography (ethyl acetate:n-hexane=4:1 v/v)

Sources & evidence

ORD record
ord-df4a11d2e61c4958901e29020ab3c37e
Source dataset
uspto-grants-2006_05
Patent number
US07045516B1

Reaction notes

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