P-Cresol → 2-(4-Methylphenoxy)-5-methyl-benzoic acid

HRID 372416

Reaction equation

HRID 372416 reaction equation
I[C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+](C1C=CC=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].[CH3:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1>[Cu].O>[CH3:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:2]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 2879P-CresolHCID 7416NitrobenzeneHCID 11430Potassium Carbonate2×HCID 1429412-Iodo-5-methylbenzoic acid

Product 1

HCID 137380552-(4-Methylphenoxy)-5-methyl-benzoic acid

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

393 G. of 2-iodo-5-methyl-benzoic acid in 150 ml. of nitrobenzene are heated to 145° C. 138 G. of potassium carbonate are added thereto in small portions with stirring. Subsequently, 156 ml. of 4-methyl-phenol and 276 g. of potassium carbonate are added. To the resulting mixture, 3 g. of copper powder are carefully added, and the mixture is subsequently stirred at 165° C. for 20 minutes. After cooling, 1.25 liters of water are added to the mixture which is then extracted twice with ether. The aqueous phase is acidified with hydrochloric acid and extracted twice with ether. The ethereal solutions are washed with water, dried over sodium sulfate and concentrated in vacuo. The residue (brown crystals) is recrystallized from 1100 ml. of methanol and 700 ml. of water, and there is obtained 2-(4-methylphenoxy)-5-methyl-benzoic acid, which after repeated recrystallization from methanol/water, melts at 113°-115° C.

Workup

  1. stirringthe mixture is subsequently stirred at 165° C. for 20 minutes
  2. temperatureAfter cooling
  3. extractionis then extracted twice with ether
  4. extractionextracted twice with ether
  5. washThe ethereal solutions are washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue (brown crystals) is recrystallized from 1100 ml

Sources & evidence

ORD record
ord-f44c1e7cb2bf448f85d4d54758772fbb
Source dataset
uspto-grants-1978_05
Patent number
US04091023

Linked notes

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