4-Phenoxyphenol → HCID 14535806, compound

HRID 2166100Notes

Reaction equation

HRID 2166100 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl.Cl[CH2:21][N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[CH:23]1>CN(C)C=O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:21][N:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[N:24]=[CH:23]2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 132544-PhenoxyphenolHCID 24758Sodium hydrideHCID 136927281-(Chloromethyl)-1H-benzimidazole--hydrogen chloride (1/1)HCID 178418361HCID 178418361, compound

Product 1

HCID 14535806HCID 14535806, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
120 °C

Procedure

At room temperature (about 20° C.) and under a nitrogen blanket, 13.95 g of p-phenoxyphenol in 100 ml of anhydrous dimethylformamide is dripped into 6.75 g of 80% strength sodium hydride in 50 ml of anhydrous dimethylformamide. Upon completion of hydrogen evolution, the mixture is stirred for 4 hours at 60° C. At 10° C., 15.22 g of 1-chloromethylbenzimidazole hydrochloride is then added. The mixture is stirred for 8 hours at 120° C. After concentration under reduced pressure, the residue is taken up in ethyl acetate, and washed three times with water and three times with 5% strength aqueous sodium hydroxide solution. The combined organic phases are dried over sodium sulfate and concentrated. The residue is recrystallized from diethyl ether. There is obtained 11.8 g of 1-[(p-phenoxyphenoxy)-methyl]-benzimidazole of m.p. 112° C.

Workup

  1. customAt room temperature
  2. custom(about 20° C.)
  3. concentrationAfter concentration under reduced pressure
  4. washwashed three times with water and three times with 5% strength aqueous sodium hydroxide solution
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-ca6f766b84d74029a1d64c0ee792bc62
Source dataset
uspto-grants-1990_07
Patent number
US04943585

Reaction notes

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