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

HRID 362840Notes

Reaction equation

HRID 362840 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-328f1ba0bfe14ab7ab4eba775acaac8c
Source dataset
uspto-grants-1999_02
Patent number
US05872118

Reaction notes

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