Nitric Acid → 1,3-Benzenedicarboxylic acid, 2-hydroxy-5-nitro-, 1,3-dimethyl ester

HRID 1268228Notes

Reaction equation

HRID 1268228 reaction equation
[OH:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[N+:16]([O-])([OH:18])=[O:17].S(=O)(=O)(O)O.O>CCCCCC>[OH:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:9]([N+:16]([O-:18])=[O:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 10889156dimethyl 2-hydroxyisophthalate

Product 1

HCID 139742081,3-Benzenedicarboxylic acid, 2-hydroxy-5-nitro-, 1,3-dimethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Dimethyl 2-hydroxyisophthalate (1.5 g) was added to a mixture of 69% nitric acid (5 ml) and concentrated sulfuric acid (5 ml) and the mixture was stirred in an ice bath for 0.5 hours. After pouring into iced water, the reaction mixture was extracted with ethyl acetate. The extract was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo to afford a yellow solid. To the solid was added hexane and the mixture was filtered to give the desired compound (1.6 g, yield 89%) as a yellow solid.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customto afford a yellow solid
  7. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-59d04821002a4ed1aada8aa5cc19c6ca
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

Loading…