Succinic anhydride → HCID 21483923, compound

HRID 1415196Notes

Reaction equation

HRID 1415196 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:7]=1[O:13][CH3:14].[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1>C(Cl)Cl>[Cl:12][C:11]1[C:6]([Cl:5])=[C:7]([O:13][CH3:14])[CH:8]=[CH:9][C:10]=1[C:15]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:21]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 161262,3-DichloroanisoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21483923HCID 21483923, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Powdered aluminum chloride (270 g., 2 moles) is added slowly at 0° C. to a stirred mixture of 2,3-dichloroanisole (177 g., 1.0 mole) and succinic anhydride (100 g., 1.0 mole) in methylene chloride (800 ml.). The mixture then is stirred at 0° C. for two hours, then at 20°-25° C. for 16 hours and then refluxed for one hour and poured into ice cold 1 N HCl (2.4 l.). The aqueous mixture is heated to 65° C. and allowed to cool to 20° C. The sticky solid that separates is triturated with warm butyl chloride to obtain 136 g. product, melting point 140°-145° C. After crystallization from ethanol-water (5:7) there is obtained 3-(2,3-dichloro-4-methoxybenzoyl)propionic acid (125 g.), melting point 142°-144° C..

Workup

  1. waitat 20°-25° C. for 16 hours
  2. temperaturerefluxed for one hour
  3. temperatureThe aqueous mixture is heated to 65° C.
  4. temperatureto cool to 20° C
  5. customThe sticky solid that separates is triturated with warm butyl chloride
  6. customto obtain 136 g
  7. customAfter crystallization from ethanol-water (5:7) there

Sources & evidence

ORD record
ord-48cefbb8827a4a24b129a9f3940b3550
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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