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

HRID 1956329Notes

Reaction equation

HRID 1956329 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].I[C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=1>CS(C)=O.[Cu]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 2879P-CresolHCID 120854-Iodobenzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 2919944-(4-Methylphenoxy)benzoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
210 °C

Procedure

To a solution of 4.36 g of 4-methyl-phenol in 70 ml of dry dimethylsulfoxide under nitrogen with stirring is added 9.0 g of potassium t-butoxide. After stirring for 15 minutes, 0.1 g of copper metal is added followed by 10.0 g of 4-iodobenzoic acid. The reactants are stirred under nitrogen while heating at 210° C. for 18 hours. The cooled reaction mixture is extracted with chloroform (2×900 ml) and the remaining water acidified with 2N HCl (pH=3) with ice bath cooling, to give 8.1 g of the desired product. MS(M+H=229.0).

Workup

  1. stirringThe reactants are stirred under nitrogen
  2. customThe cooled reaction mixture
  3. extractionis extracted with chloroform (2×900 ml)
  4. customthe remaining water acidified with 2N HCl (pH=3) with ice bath
  5. temperaturecooling

Sources & evidence

ORD record
ord-f22b9def5b354e719906590b61fc026d
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

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