Water → HCID 53873583, compound

HRID 263470Notes

Reaction equation

HRID 263470 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].O.[C:17](OCC)(=[O:19])[CH3:18]>C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>[C:17]([O:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14])(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 534017683-(4-Hydroxy-3-nitrophenyl)prop-2-enoic acid

Product 1

HCID 53873583HCID 53873583, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

10 g of 4-hydroxy-3-nitrocinnamic acid (prepared as described in Preparation 1) were dissolved in 30 ml of acetic anhydride. One drop of sulfuric acid was added to the solution, which was then stirred for 2 hours at room temperature. 50 ml of water were added the solution, and it was then stirred for a further 2 hours. At the end of this time, ethyl acetate was added, and the mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order, and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was mixed with toluene; the remaining acetic acid was removed by azeotropic distillation to obtain 10.2 g of the title compound as crystals.

Workup

  1. stirringwas then stirred for a further 2 hours
  2. washthe mixture was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. additionthe residue was mixed with toluene
  6. customthe remaining acetic acid was removed by azeotropic distillation

Sources & evidence

ORD record
ord-98b3f75389d14d12a14eb31b8910e4ca
Source dataset
uspto-grants-1997_07
Patent number
US05643925

Reaction notes

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