P-Cresol → 2-(4-Methylphenoxy)benzoic acid

HRID 466427Notes

Reaction equation

HRID 466427 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([CH3:8])[CH:2]=1.[C:9](=[O:12])([O-])[O-:10].[K+].[K+]>CN(C)C=O.[Cu]I>[CH3:8][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[C:9]([OH:10])=[O:12])=[CH:1][CH:2]=1

Participants

5

Reactant 2

HCID 2879P-CresolHCID 11430Potassium Carbonate

Product 1

HCID 5786562-(4-Methylphenoxy)benzoic acidYield 90.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.95 g of p-cresol and 7.83 g of 2-chlorobenzoic in 50 mL of dimethylformamide at 25° was added, in portions, 14.50 g of anhydrous potassium carbonate. The resulting mixture was heated to 80°, and 0.10 g of copper(I) iodide was added. The reaction mixture then was refluxed for 16 hours. While still hot the mixture was poured onto water-ice. The resulting suspension was filtered, and the filtrate was adjusted to pH 3.0 using aqueous hydrochloric acid. The precipitate was recovered by filtration. The crude solid was dissolved in an aqueous sodium hydroxide solution. This solution was acidified to pH 6.0 using hydrochloric acid, filtered, and then acidified to pH 3.0. Filtration provided 5.67 g of 2-(4-methylphenoxy)benzoic acid which was employed in the following reaction without further purification. NMR (200 MHz, CDCl3): δ 8.15 (d of d, 1H); 7.42 (d of d of d, 1H); 7.23-7.12 (m, 3H); 6.97 (d, 2H); 6.80 (d, 1H); 2.37 (s, 3H).

Workup

  1. temperatureThe resulting mixture was heated to 80°
  2. temperatureThe reaction mixture then was refluxed for 16 hours
  3. additionWhile still hot the mixture was poured onto water-ice
  4. filtrationThe resulting suspension was filtered
  5. filtrationThe precipitate was recovered by filtration
  6. dissolutionThe crude solid was dissolved in an aqueous sodium hydroxide solution
  7. filtrationfiltered
  8. filtrationFiltration

Sources & evidence

ORD record
ord-a4101d845a1b4949b778e2b3202d6925
Source dataset
uspto-grants-1992_10
Patent number
US05155118

Reaction notes

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