Potassium Hydroxide → 3-(4-Fluorophenyl)pentanoic acid

HRID 1954920Notes

Reaction equation

HRID 1954920 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:15][CH3:16])[CH2:9][C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[K+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:15][CH3:16])[CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23293610Ethyl 3-(4-fluorophenyl)valerate

Product 1

HCID 232935663-(4-Fluorophenyl)pentanoic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared in an analogous manner to Example 18c with the replacement of 3-(4-fluorophenyl)butyrate with ethyl 3-(4-fluorophenyl)valerate (38.95 g 0.144 mol, containing 29% triethyl phosphoneacetate) and using an excess of 85% potassium hydroxide (18.05 g, 0.273 mol, Mallinckrodt). The dichloromethane layers were combined, washed with deionized water (50 ml) and concentrated by spin evaporation in vacuo. The residue was crystallized from hexanes to give 23.47 g (83%) of 3-(4-fluorophenyl)valeric acid as a white crystalline solid: NMR (DMSO-d6): d 12 (s, 1H), 7.28-7.24 (m, 2H), 7.14-7.08 (m, 2H), 2.91-2.89 (m, 1H), 2.64-2.41 (m, 2H), 1.66-162 (m, 1H), 1.56-1.51 (m, 1H), 0.71 (t, 3H, J=7.3 Hz).

Workup

  1. washwashed with deionized water (50 ml)
  2. concentrationconcentrated by spin evaporation in vacuo
  3. customThe residue was crystallized from hexanes

Sources & evidence

ORD record
ord-5077bf2e8a2245eabf3198c3c557bad9
Source dataset
uspto-grants-2000_09
Patent number
US06124284

Reaction notes

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