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

HRID 2373206Notes

Reaction equation

HRID 2373206 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11][C:12]([CH3:14])=[O:13].CC(O)=O.N1CCCCC1>C1CCCCC1.CCOC(C)=O>[C:12]([C:11](=[CH:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[CH:3]=1)[C:10]([O:16][CH2:17][CH3:18])=[O:15])(=[O:13])[CH3:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 114773-Chlorobenzaldehyde

Product 1

HCID 367058Ethyl 2-acetyl-3-(3-chlorophenyl)acrylateYield 116.5%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-chlorobenzaldehyde (2 g), ethyl acetoacetate (1.94 g), AcOH (0.23 ml), piperidine (0.23 ml) in cyclohexane (40 ml) was refluxed azeotropically for 2 hours. After cooling, the reaction mixture was diluted with EtOAc. The organic layer was washed with water, saturated aqueous NaHCO3, brine, dried over anhydrous MgSO4 and concentrated in vacuo to give ethyl 2-acetyl-3-(3-chlorophenyl)acrylate (4.19 g) as a yellow oil.

Workup

  1. temperaturewas refluxed azeotropically for 2 hours
  2. temperatureAfter cooling
  3. washThe organic layer was washed with water, saturated aqueous NaHCO3, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd5177f6f0ce4c66ba09eb41c6173155
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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