Nitric Acid → 1,3-Dimethyl-2,4-dinitrobenzene

HRID 1284958Notes

Reaction equation

HRID 1284958 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N+:9]([O-:11])=[O:10].S(=O)(=O)(O)O.[N+:17]([O-])([OH:19])=[O:18].O>C(Cl)Cl>[CH3:8][C:4]1[CH:5]=[CH:6][C:7]([N+:17]([O-:19])=[O:18])=[C:2]([CH3:1])[C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 1118Sulfuric Acid2×HCID 66722,6-Dimethylnitrobenzene

Product 1

HCID 690421,3-Dimethyl-2,4-dinitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-dimethyl-2-nitrobenzene (151.2 g) is dissolved in 500 ml of CH2Cl2 and cooled to below 0° C. in a methanol ice bath. Sulfuric acid (200 ml) is added dropwise maintaining a temperature at below 0° C. After the sulfuric acid addition is complete, fuming nitric acid (86 ml) is added dropwise at a rate which maintains the temperature between -5° to -2° C. After the addition is complete the mixture is stirred at -3° to -5° C. for 2 hours. 200 ml of water are carefully added to the aqueous acidic layer and after cooling to room temperature is extracted with 600 ml of CH2Cl2. The extracts are combined and washed with 600 ml of H2O saturated NaCl solution and dried overnight. The mixture is filtered and the filtrate concentrated to give 192.2 grams of a yellow solid, M.P. 81°-83° C.

Workup

  1. temperaturecooled to below 0° C. in a methanol ice bath
  2. temperaturemaintaining a temperature at below 0° C
  3. custombetween -5° to -2° C
  4. additionAfter the addition
  5. extractionis extracted with 600 ml of CH2Cl2
  6. washwashed with 600 ml of H2O saturated NaCl solution
  7. customdried overnight
  8. filtrationThe mixture is filtered
  9. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-d5e522786f964593aa2cc750b09dff72
Source dataset
uspto-grants-1986_01
Patent number
US04564640

Reaction notes

Loading…