Acetoacetic Acid → Ethyl 2-acetyl-3-(3-chlorophenyl)acrylate

HRID 1182614Notes

Reaction equation

HRID 1182614 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O.N1CCC[CH2:19][CH2:18]1.C(O)(=O)C>CC(O)C>[CH2:18]([O:6][C:1](=[O:7])[C:2]([C:3](=[O:4])[CH3:5])=[CH:12][C:11]1[CH:14]=[CH:15][CH:16]=[C:9]([Cl:8])[CH:10]=1)[CH3:19]

Participants

6

Reactant 4

HCID 96Acetoacetic AcidHCID 176Acetic AcidHCID 8082PiperidineHCID 114773-Chlorobenzaldehyde

Product 1

HCID 367058Ethyl 2-acetyl-3-(3-chlorophenyl)acrylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5.00 g (38.4 mmol) of acetoacetic acid and 5.40 g (38.4 mmol) of 3-chlorobenzaldehyde were dissolved in 50 ml of 2-propanol. 327 mg (3.84 mmol) of piperidine and 231 mg (3.84 mmol) of acetic acid were added and stirred at room temperature for one day. After the solvent was evaporated, ethyl acetate was added and the reaction mixture was washed with 1 N hydrochloric acid and saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=5/1) to obtain the title compound.

Workup

  1. customAfter the solvent was evaporated
  2. additionethyl acetate was added
  3. washthe reaction mixture was washed with 1 N hydrochloric acid and saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e37709e1ff6849969879df67f2810208
Source dataset
uspto-grants-2007_10
Patent number
US07288544B2

Reaction notes

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