Water → alpha-Methoxy-beta-[4-(4-trifluoromethylphenoxy)phenoxy]propane

HRID 2419158Notes

Reaction equation

HRID 2419158 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:20]=[CH:19][C:6]([O:7][C:8]2[CH:18]=[CH:17][C:11]([O:12][CH:13]([CH3:16])[CH2:14][OH:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[Na].[CH3:24]I.O>O1CCOCC1>[CH3:24][O:15][CH2:14][CH:13]([O:12][C:11]1[CH:17]=[CH:18][C:8]([O:7][C:6]2[CH:19]=[CH:20][C:3]([C:2]([F:21])([F:22])[F:1])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1)[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 5360545SodiumHCID 128048852-{4-[4-(Trifluoromethyl)phenoxy]phenoxy}propan-1-ol

Product 1

HCID 23332249alpha-Methoxy-beta-[4-(4-trifluoromethylphenoxy)phenoxy]propaneYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

6 g of β-[4-(4-trifluoromethylphenoxy)phenoxy]propanol was dissolved in 30 ml of dioxane and 0.46 g of sodium was added to the solution. The mixture was then heated for 3 hours while refluxing. 3.1 g of methyl iodide was added thereto and the resulting mixture was heated for 6 hours while refluxing. The reaction mixture was then poured into an appropriate amount of water and extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulfate. The ether was removed by distillation and the residue was distilled under reduced pressure to obtain 4.2 g of the desired product having a boiling point of 160° to 165° C/2 mmHg.

Workup

  1. temperatureThe mixture was then heated for 3 hours
  2. temperaturewhile refluxing
  3. temperaturethe resulting mixture was heated for 6 hours
  4. temperaturewhile refluxing
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe ether was removed by distillation
  9. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-5ac17d9642054ae297491504eae5d148
Source dataset
uspto-grants-1978_08
Patent number
US04105435

Reaction notes

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