Nitric Acid → 1,2,3-Trimethoxy-5-nitrobenzene

HRID 495486Notes

Reaction equation

HRID 495486 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:11][CH3:12])=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.[N+:13]([O-])([OH:15])=[O:14]>CC(O)=O>[CH3:10][O:9][C:5]1[CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 124621,2,3-Trimethoxybenzene

Product 1

HCID 2387701,2,3-Trimethoxy-5-nitrobenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Trimethoxybenzene (100 g, 0.594 mol) was dissolved in AcOH (220 mL) and stirred while adding 70% HNO3 (69 mL, 1.088 mol) over 20 min. The temperature was kept at 70° C. by cooling as necessary in a water bath. The cooling bath was removed after addition and the mixture remained at 65° C. for several min before cooling. Ice/water was added to precipitate a solid product which was washed well with water. 1M NaOH (500 mL) was added and stirred with the solid for 5 min. The solid was collected, washed with water until the washings were colorless and dried in air, giving 3,4,5-trimethoxynitrobenzene as pale yellow needles.

Workup

  1. customwas kept at 70° C.
  2. temperatureby cooling as necessary in a water bath
  3. customThe cooling bath was removed
  4. additionafter addition
  5. customremained at 65° C. for several min
  6. temperaturebefore cooling
  7. additionIce/water was added
  8. customto precipitate a solid product which
  9. washwas washed well with water
  10. addition1M NaOH (500 mL) was added
  11. stirringstirred with the solid for 5 min
  12. customThe solid was collected
  13. washwashed with water until the washings
  14. customdried in air

Sources & evidence

ORD record
ord-8bd39ccd36874e2fa03333b9ea0e1806
Source dataset
uspto-grants-2005_09
Patent number
US06939874B2

Reaction notes

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