Acetic Anhydride → Ethyl 4-acetoxynaphthalene-2-carboxylate

HRID 1185455Notes

Reaction equation

HRID 1185455 reaction equation
C(O[C:4](=O)[C:5](=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.C([O-])(=O)C.[Na+].[C:24]([O:27][C:28](=O)C)(=[O:26])[CH3:25]>O>[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[C:28]([O:27][C:24](=[O:26])[CH3:25])[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=1)=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 94751Diethyl (phenylmethylene)malonateHCID 517045Sodium Acetate

Product 1

HCID 364908Ethyl 4-acetoxynaphthalene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 24 g of 2-Benzylidene-malonic acid diethyl ester in 60 ml of acetic acid anhydride, 7.5 g 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 pure enough for the next reaction step.

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 pure enough for the next reaction step

Sources & evidence

ORD record
ord-cd19bca7f0ba4f45aba9fdc76ba0c16d
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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