Hydrochloric Acid → 3-(4-Fluorobenzoyl)propionic acid

HRID 862773Notes

Reaction equation

HRID 862773 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(=[O:14])[O:13][C:11](=[O:12])[CH2:10][CH2:9]1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC1C=CC=CC=1Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:14])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7922Succinic anhydrideHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1013593-(4-Fluorobenzoyl)propionic acidYield 89.9%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of fluorobenzene (104.4 g, 1.09 mol, Aldrich) and succinic anhydride (93.5 g, 0.93 mol) in 1,2-dichlorobenzene (530 mL) was heated to 50° C. Aluminum chloride (245 g, 1.84 mol) was added portionwise keeping the temperature below 60° C. After 4 h at 60° C. followed by 5 h at 80° C., the reaction mixture was poured into a mixture of concentrated HCl (200 mL) and ice water (2 L). The organic layer was separated and the aqueous phase was extracted with dichloromethane. The combined organic phase was dried and concentrated in vacuo. The residue was poured into hexane (2 L) and the resulting solid was filtered and washed with pentane to give 164.1 g (89%) of 3-(4-fluorobenzoyl)propionic acid as a white solid. m.p., 102°-104.5° C. (lit J. Org. Chem. 26, 2667, 1961; m.p., 102.5°-103.5° C.)

Workup

  1. customthe temperature below 60° C
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. customThe combined organic phase was dried
  5. concentrationconcentrated in vacuo
  6. additionThe residue was poured into hexane (2 L)
  7. filtrationthe resulting solid was filtered
  8. washwashed with pentane

Sources & evidence

ORD record
ord-4b93845bdebd4c03aa1d81c958f1f853
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

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