Sodium Acetate → HCID 68599246, compound

HRID 1185503Notes

Reaction equation

HRID 1185503 reaction equation
[CH2:1]([O:3][C:4](=[O:20])/[C:5](=[CH:12]/[C:13]1[CH:14]=[C:15]([CH3:19])[CH:16]=[CH:17][CH:18]=1)/[CH2:6][C:7]([O:9][CH2:10][CH3:11])=O)[CH3:2].C([O-])(=[O:23])C.[Na+]>C(OC(=O)C)(=O)C.O>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([O:9][C:10](=[O:23])[CH3:11])[C:18]2[C:13](=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=2)[CH:12]=1)=[O:20])[CH3:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 685999652-[1-m-Tolyl-meth-(e)-ylidene]-succinic acid diethyl ester

Product 1

HCID 68599246HCID 68599246, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 2 g of 2-[1-m-Tolyl-meth-(E)-ylidene]-succinic acid diethyl ester in 10 ml of acetic acid anhydride, 594 mg sodium acetate was added and the reaction mixture was heated to reflux for 5 h. After cooling to RT the reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were washed three times with saturated aqueous sodium hydrogen carbonate solution. The organic phase was dried over MgSO4 and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate (1/1). The fractions containing the product were combined and the solvent evaporated under reduced pressure. Yield: 860 mg.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed three times with saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvents were removed under reduced pressure
  7. customThe crude product was purified by chromatography on silica gel eluting with n-heptane/ethyl acetate (1/1)
  8. additionThe fractions containing the product
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-3e1f709694944f8c88086839924f237f
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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