Diethyl (2,4-dichloro-3,6-difluorobenzoyl)-malonate → Ethyl (2,4-dichloro-3,6-difluorobenzoyl)acetate

HRID 36709

Reaction equation

HRID 36709 reaction equation
[Cl:1][C:2]1[C:20]([F:21])=[C:19]([Cl:22])[CH:18]=[C:17]([F:23])[C:3]=1[C:4]([CH:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]>O>[Cl:1][C:2]1[C:20]([F:21])=[C:19]([Cl:22])[CH:18]=[C:17]([F:23])[C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

3

Reactant 1

HCID 15070034Diethyl (2,4-dichloro-3,6-difluorobenzoyl)-malonate

Product 1

HCID 15070035Ethyl (2,4-dichloro-3,6-difluorobenzoyl)acetateYield 49.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.04 g of p-toluenetoluenesulphonic acid is added to an emulsion of 34.7 g of crude diethyl (2,4-dichloro-3,6-difluorobenzoyl)-malonate in 40 ml of water. The mixture is heated at the boiling point for 3 hours, while stirring thoroughly, the cooled emulsion is extracted several times with methylene chloride, the combined CH2Cl2 solutions are washed once with saturated sodium chloride solution and dried with Na2SO4 and the solvent is distilled off in vacuo. Fractionation of the residue (33.9 g) in vacuo gives 13.9 g of ethyl (2,4-dichloro-3,6-difluorobenzoyl)-acetate of boiling point 110°-115° C./0.05 mbar, nD25 : 1,5241.

Workup

  1. temperatureThe mixture is heated at the boiling point for 3 hours
  2. extractionthe cooled emulsion is extracted several times with methylene chloride
  3. washthe combined CH2Cl2 solutions are washed once with saturated sodium chloride solution
  4. dry with materialdried with Na2SO4
  5. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-85d2a1a297be4b2a927b6c639d4588a1
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Linked notes

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