Methane → HCID 12650295, compound

HRID 1605168Notes

Reaction equation

HRID 1605168 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C>O.[Cu].CN(C)C=O>[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 2879P-CresolHCID 57872,4-Dichlorobenzoic AcidHCID 11430Potassium Carbonate

Product 1

HCID 12650295HCID 12650295, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 15 g. of 2,4-dichlorobenzoic acid, 10 g. of p-methylphenol, 0.5 g. of copper powder and 20 g. of anhydrous potassium carbonate in 200 ml. of dimethylformamide is heated to 165° C and maintained thereat with stirring and under a nitrogen atmosphere. After monitoring via tlc indicates the reaction is substantially complete, the reaction mixture is diluted with water, treated with charcoal, filtered and the clear filtrate acidified. The precipitate is isolated by suction filtration, washed neutral and dried to give 2-(p-methylphenyloxy)-4-chlorobenzoic acid.

Workup

  1. additionA mixture of 15 g
  2. temperaturemaintained
  3. filtrationfiltered
  4. customThe precipitate is isolated by suction filtration
  5. washwashed neutral
  6. customdried

Sources & evidence

ORD record
ord-ea08849779bf48ec85d709fd9f0fa43b
Source dataset
uspto-grants-1976_04
Patent number
US03949084

Reaction notes

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