Sulfuric Acid → HCID 22457396, compound

HRID 2184632Notes

Reaction equation

HRID 2184632 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.[CH:21]1(O)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([O:15][CH:4]2[CH2:5][CH2:6][CH2:7][CH2:11][CH2:12]2)=[O:14])[C:7](=[CH:11][CH:12]=1)[C:8]([O:10][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:9])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7966CyclohexanolHCID 691211,2-Benzenedicarboxylic acid, 4-nitro-

Product 1

HCID 22457396HCID 22457396, compoundYield 65.5%

Conditions

Temperature
120 °C

Procedure

4-nitrophthalic acid (2.0 g, 9.5 mmol) was dissolved in 30 ml of cyclohexanol, and then 0.3 ml of conc. 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, the residue was purified by silica gel column chromatography (n-hexane: acetic acid =10:1) to give 2.3 g (65.5%) of dicyclohexyl 4-nitrophthalate (compound 405).

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. customthe residue was purified by silica gel column chromatography (n-hexane: acetic acid =10:1)

Sources & evidence

ORD record
ord-683153cfaf004c4c9561722dc0982e81
Source dataset
uspto-grants-2002_06
Patent number
US06399318B1

Reaction notes

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