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

HRID 703663Notes

Reaction equation

HRID 703663 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]>N1C=CC=CC=1.C(O)(=O)CCCCC.C1C=CC=CC=1>[CH3:18][O:17][C:11](=[O:16])[C:12](=[CH:4][C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:2]=1[Cl:1])[C:13](=[O:14])[CH3:15]

Participants

6

Reactant 2

HCID 7757Methyl acetoacetateHCID 357452,3-Dichlorobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 3

HCID 1049PyridineCatalystHCID 8892Hexanoic AcidCatalystHCID 241BenzeneSolvent

Procedure

A mixture containing 8.7 g of 2,3-dichlorobenzaldehyde, 5.8 g of methyl acetoacetate, 28 drops of pyridine and 38 drops of hexanoic acid in 280 ml of benzene is brought to reflux with stirring for 4 hours. It is transferred to a separating funnel and washed with 10% strength sodium bicarbonate solution, then with N hydrochloric acid solution and then with water. The mixture is dried and evaporated. The crystals obtained are washed with isopropyl ether.

Workup

  1. temperatureto reflux
  2. customIt is transferred to a separating funnel
  3. washwashed with 10% strength sodium bicarbonate solution
  4. customThe mixture is dried
  5. customevaporated
  6. customThe crystals obtained
  7. washare washed with isopropyl ether

Sources & evidence

ORD record
ord-ea88266d1368437abdc5f08d16a38e78
Source dataset
uspto-grants-1991_01
Patent number
US04983740

Reaction notes

Loading…