Nitric Acid → HCID 23452882, compound

HRID 2049910Notes

Reaction equation

HRID 2049910 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:13]=[CH:12][CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.C(Cl)Cl.[N+:18]([O-])([OH:20])=[O:19].C(OCC)(=[O:24])C>>[OH:24][C:12]1[CH:13]=[C:4]([C:3]([O:2][CH3:1])=[O:14])[C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 15088Dimethyl isophthalate

Product 1

HCID 23452882HCID 23452882, compound

Procedure

To a suspension of 60 g. of dimethylisophthalate in 600 ml. of methylene chloride are added 200 ml. of concentrated nitric acid, and the mixture is rapidly stirred at room temperature for about 45 min. After this time, 300 ml. of ice water are added, followed by 700 ml. of ethyl acetate. The organic layer is separated, washed with two portions of saturated brine, and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure, leaving a sticky solid which is triturated with 100 ml. of warm benzene. The insoluble material is collected and washed with benzene to give 19.5 g. (27%) of white to pale yellow solid, m.p. 183°-186° C.

Workup

  1. additionTo a suspension of 60 g
  2. customThe organic layer is separated
  3. washwashed with two portions of saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customleaving a sticky solid which
  7. customis triturated with 100 ml
  8. customThe insoluble material is collected
  9. washwashed with benzene
  10. customto give 19.5 g

Sources & evidence

ORD record
ord-607e337e21d343d2a38596092a755640
Source dataset
uspto-grants-1980_04
Patent number
US04199354

Reaction notes

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