Potassium Permanganate → 2'-Trifluoromethyl (1,1'-biphenyl)-4-carboxylic acid

HRID 710376Notes

Reaction equation

HRID 710376 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=1.[O-:19][Mn](=O)(=O)=O.[K+]>O1CCOCC1>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:19])=[O:16])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 13926532'-TrifluoroMethyl-Biphenyl-4-Carbaldehyde

Product 1

HCID 27827142'-Trifluoromethyl (1,1'-biphenyl)-4-carboxylic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A suspension of the product of step A (0.4 g, 1.6 mmol) and KMnO4 (0.502 g, 3.2 mmol) in dioxane (15 ml) was refluxed for 2 h with stirring. The solution was filtered through silica gel bead and washed with EtOAc (30 ml). The solvent was evaporated to dryness to give the title compound (0.35 g, 81.6%), as white solid. 1H-NMR (CDCl3) 7.30-7.58 (m, 5H); 7.76 (d, 1H, J=8.15 Hz); 8.11 (d, 2H, J=8.03 Hz).

Workup

  1. temperaturewas refluxed for 2 h
  2. filtrationThe solution was filtered through silica gel bead
  3. washwashed with EtOAc (30 ml)
  4. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-b9a3c51d27e54c77b0a0af04b3e11653
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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