Water → Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester

HRID 1857369Notes

Reaction equation

HRID 1857369 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:11]([O:17][CH3:18])(=[O:16])[CH2:12][C:13]([CH3:15])=[O:14].O.N1CCCCC1>C(Cl)Cl.CC(O)=O>[C:13]([C:12](=[CH:4][C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:2]=1[Cl:1])[C:11]([O:17][CH3:18])=[O:16])(=[O:14])[CH3:15]

Participants

7

Reactant 4

HCID 962WaterHCID 7757Methyl acetoacetateHCID 8082PiperidineHCID 357452,3-Dichlorobenzaldehyde

Product 1

HCID 54242386Butanoic acid, 2-[(2,3-dichlorophenyl)methylene]-3-oxo-, methyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

17.5 g (100 mmol) of 2,3-dichlorobenzaldehyde and 11.6 g (100 mmol) of methyl acetoacetate are boiled in a water separator for 3 h with 1 ml of piperidine and 0.5 ml of HOAc in 350 ml of CH2Cl2. The mixture is then washed twice with water, dried over MgSO4 and concentrated. The residue crystallizes from petroleum ether/ether. Yield: 15.0 g (55%)

Workup

  1. washThe mixture is then washed twice with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue crystallizes from petroleum ether/ether

Sources & evidence

ORD record
ord-fe47c5ef738b4b0ba637b2c480b1fe2a
Source dataset
uspto-grants-2000_11
Patent number
US06147087

Reaction notes

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