Succinic anhydride → 4-[3-Chloro-4-(ethoxycarbonylmethoxy)phenyl]-4-oxobutyric acid

HRID 2072684

Reaction equation

HRID 2072684 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1.[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[Cl:1][C:2]1[CH:14]=[C:13]([C:15](=[O:21])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 302826Ethyl 2-(2-chlorophenoxy)acetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 148782884-[3-Chloro-4-(ethoxycarbonylmethoxy)phenyl]-4-oxobutyric acidYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

12.9 g of ethyl 2-chlorophenoxyacetate (prepared as described in Preparation 1) and 6.00 g of succinic anhydride were dissolved in 70 ml of methylene chloride, and 25.2 g of aluminum trichloride were added thereto in small portions at 0°-5° C., with stirring. The mixture was then stirred at room temperature for 3 hours, poured into ice-water and then extracted with ethyl acetate. The extract was washed with water and dried. The solvent was distilled off in vacuo and the resulting precipitate was recrystallized from a mixture of ethyl acetate and hexane, to give 14.3 g of the title compound melting at 137°-139° C.

Workup

  1. stirringThe mixture was then stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. distillationThe solvent was distilled off in vacuo
  6. customthe resulting precipitate was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-dfa9589966ea4a618e0a2d674cb6d54e
Source dataset
uspto-grants-1990_04
Patent number
US04914093

Linked notes

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