Water → HCID 53873583, compound

HRID 977089Notes

Reaction equation

HRID 977089 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-b081a7d4bf8f4b9a95c74d12d050d0bf
Source dataset
uspto-grants-1997_03
Patent number
US05614521

Reaction notes

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