Sulfuric Acid → HCID 20288523, compound

HRID 126936Notes

Reaction equation

HRID 126936 reaction equation
[C:1]([C:9]1[C:10]([N+:23]([O-:25])=[O:24])=[C:11]([C:15](C)([C:19](O)=O)[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>C(O)(=O)C>[C:1]([C:9]1[C:10]([N+:23]([O-:25])=[O:24])=[C:11]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 20288512HCID 20288512, compound

Product 1

HCID 20288523HCID 20288523, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.0 g (0.0075 mole) of 2-(3-benzoyl-2-nitrophenyl)-2-methylpropanedioic acid, 20 ml of acetic acid and 20 ml of 20% sulfuric acid was heated at reflux under a nitrogen atomsphere overnight. The dark solution was concentrated and the residue was treated with 200 ml of 2N potassium carbonate. The mixture was triturated with diethyl ether and then filtered to remove insoluble material. The filtrate layers were separated and the aqueous layer was washed with diethylether. The aqueous solution was treated with charcoal, filtered through celite and the filtrate made acidic with 13 ml of conc. sulfuric acid. The solid which precipitated was collected by filtration and recrystallized from 2-propanol-water to yield 0.4 g (18%) of white powder, m.p. 177°-179° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atomsphere overnight
  3. concentrationThe dark solution was concentrated
  4. additionthe residue was treated with 200 ml of 2N potassium carbonate
  5. customThe mixture was triturated with diethyl ether
  6. filtrationfiltered
  7. customto remove insoluble material
  8. customThe filtrate layers were separated
  9. washthe aqueous layer was washed with diethylether
  10. additionThe aqueous solution was treated with charcoal
  11. filtrationfiltered through celite
  12. customThe solid which precipitated
  13. filtrationwas collected by filtration
  14. customrecrystallized from 2-propanol-water

Sources & evidence

ORD record
ord-b267bd199e384193b1c3c4a9296c2cd5
Source dataset
uspto-grants-1981_03
Patent number
US04254146

Reaction notes

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