Succinic anhydride → 3-(4-Fluorobenzoyl)propionic acid

HRID 358385Notes

Reaction equation

HRID 358385 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12]1(=[O:18])[O:17][C:15](=[O:16])[CH2:14][CH2:13]1>>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:18])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 7922Succinic anhydrideHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1013593-(4-Fluorobenzoyl)propionic acid

Procedure

A suspension of 170 g anhydrous aluminum chloride and 266 g fluorobenzene was stirred under nitrogen at 10° C. while succinic anhydride (54.4 g) was added in small portions. The mixture was stirred 1.5 hours at 10° to 20° C. and then heated on a steam bath for 45 minutes. The mixture was poured onto 1.2 kg crushed ice containing 280 ml 6N HCl. The product was extracted into methylene chloride, which was washed with water, and then back-extracted into 2N NaOH. The basic extract was treated with activated carbon, and acidified with HCl to precipitate title product, 94 g, mp 98.5°-101° C. Recrystallization from methylene chloride/hexane gave 90.6% recovery, mp 99°-101° C.

Workup

  1. additionwas added in small portions
  2. temperatureheated on a steam bath for 45 minutes
  3. additionThe mixture was poured onto 1.2 kg
  4. extractionThe product was extracted into methylene chloride, which
  5. washwas washed with water
  6. extractionback-extracted into 2N NaOH
  7. extractionThe basic extract
  8. additionwas treated with activated carbon
  9. customto precipitate title product, 94 g, mp 98.5°-101° C
  10. customRecrystallization from methylene chloride/hexane
  11. customgave 90.6% recovery, mp 99°-101° C.

Sources & evidence

ORD record
ord-1f520951104040c0af3a7290ec07916d
Source dataset
uspto-grants-1984_08
Patent number
US04467090

Reaction notes

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