Sulfuric Acid → HCID 22457397, compound

HRID 2184630Notes

Reaction equation

HRID 2184630 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([OH:15])=[O:14])[C:7](=[CH:11][CH:12]=1)[C:8]([OH:10])=[O:9])([O-:3])=[O:2].S(=O)(=O)(O)O>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([O:15][CH2:13][CH2:6][CH2:7][CH3:8])=[O:14])[C:7](=[CH:11][CH:12]=1)[C:8]([O:10][CH2:5][CH2:4][CH2:12][CH3:11])=[O:9])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 691211,2-Benzenedicarboxylic acid, 4-nitro-

Product 1

HCID 22457397HCID 22457397, compoundYield 136.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

4-nitrophthalic acid (2.0 g, 9.5 mmol) was dissolved in 30 ml of absolute ethanol and then 0.3 ml of concentrated sulfuric acid was added. The mixture was heated at 120° C. for 24 hours, and the solvent was evaporated under reduced pressure. The oily residue was dissolved in diethyl ether and washed three times with water and once with 10% Na2CO3 solution. The ether solution was dried over anhydrous sodium sulfate. After evaporation of the solvent, a light yellow crude solid was obtained. The crude product was purified by silica gel column chromatography (n-hexane: acetic acid =10:1) to give 2.1 g (68.4%) of di-n-butyl 4-nitrophthalate (compound 403).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe oily residue was dissolved in diethyl ether
  3. washwashed three times with water
  4. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  5. customAfter evaporation of the solvent
  6. customa light yellow crude solid was obtained
  7. customThe crude product was purified by silica gel column chromatography (n-hexane: acetic acid =10:1)

Sources & evidence

ORD record
ord-128edfc196634d60801854f711646ac2
Source dataset
uspto-grants-2002_06
Patent number
US06399318B1

Reaction notes

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