3-(Trifluoromethyl)phenol → HCID 70652002, compound

HRID 2401697Notes

Reaction equation

HRID 2401697 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH2:14]([O:16][CH2:17]Cl)[CH3:15]>CN(C=O)C>[CH2:14]([O:16][CH2:17][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)[CH3:15]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 18523Chloromethyl ethyl etherHCID 24758Sodium hydride

Product 1

HCID 70652002HCID 70652002, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A mixture of 10 g of 3-(trifluoromethyl)phenol and 15 ml of DMF was added dropwise to a mixture of 2.71 g of sodium hydride (60%, oil-based) and 45 ml of DMF under ice-cooling, and the mixture was stirred for 30 minutes. Subsequently, a mixture of 7.0 g of chloromethyl ethyl ether and 5 ml of DMF was added dropwise thereto, and the mixture was stirred for 1 hour. The reaction mixture was added to ice water. This mixture was extracted twice with ethyl acetate. The organic layers were combined and washed with water and saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure, to obtain 13 g of 1-ethoxymethoxy-3-(trifluoromethyl)benzene.

Workup

  1. temperaturecooling
  2. additionwas added dropwise
  3. stirringthe mixture was stirred for 1 hour
  4. extractionThis mixture was extracted twice with ethyl acetate
  5. washwashed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c0f8fe443ce4be9b7578ab93baa1776
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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