Potassium Hydroxide → 3-(4-fluorophenyl)butanoic acid

HRID 1954903Notes

Reaction equation

HRID 1954903 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:15])[CH2:9][C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[K+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:15])[CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 11160124Ethyl 3-(4-fluorophenyl)butyrate

Product 1

HCID 2919153-(4-fluorophenyl)butanoic acidYield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of ethyl 3-(4-fluorophenyl)butyrate (45.3 g, 0.215 mol), 85% potassium hydroxide (14.22 g, 0.215 mol, Mallinckrodt) in 200 ml of deionized water was refluxed for 2 h, concentrated by spin evaporation in vacuo, made acidic (pH 3) with 12 N hydrochloric acid (Mallinckrodt), and extracted with dichloromethane (4×200 ml). The dichloromethane layers were combined, washed with deionized water (50 ml), and concentrated by spin evaporation in vacuo. The residue was crystallized from dichloromethane-hexanes to give 34.5 g (88%) of 3-(4-fluorophenyl)butyric acid as a white crystalline solid:

Workup

  1. concentrationconcentrated by spin evaporation in vacuo
  2. extractionextracted with dichloromethane (4×200 ml)
  3. washwashed with deionized water (50 ml)
  4. concentrationconcentrated by spin evaporation in vacuo
  5. customThe residue was crystallized from dichloromethane-hexanes

Sources & evidence

ORD record
ord-22ccd13ea5704a99af3802d254755a53
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

Loading…