3-(Trifluoromethyl)phenol → HCID 14097612, compound

HRID 569512Notes

Reaction equation

HRID 569512 reaction equation
C[O-].[Na+].[F:4][C:5]([F:14])([F:13])[C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.Cl[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1>CO>[F:4][C:5]([F:13])([F:14])[C:6]1[CH:7]=[C:8]([CH:9]=[CH:10][CH:11]=1)[O:12][CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 203942-(Chloromethyl)quinolineHCID 10942334Sodium Methoxide

Product 1

HCID 14097612HCID 14097612, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide (1.67 g, 30.84 mmol) in 100 ml of methanol is added 3-trifluoromethylphenol (3.75 ml, 30.84 mmol). After thirty minutes the solvent is removed in vacuo and replaced by 150 ml dimethylformamide. After addtion of 2-(chloromethyl)quinoline (5.48 g, 30.85 mmol) the reaction mixture is stirred overnight. The solvent is then removed and the residue is partitioned between water and chloroform. The organic layer is dried over sodium sulfate and the solvent is removed. The residue is passed through a silica gel column (eluting with 5:1 hexane-ethyl acetate) and then recrystallized from toluene to afford white crystals (1.4 g, 15%), m.p. 77°-78° C.

Workup

  1. customAfter thirty minutes the solvent is removed in vacuo
  2. customThe solvent is then removed
  3. customthe residue is partitioned between water and chloroform
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customthe solvent is removed
  6. washThe residue is passed through a silica gel column (eluting with 5:1 hexane-ethyl acetate)
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-5f0c205e8bac4e30aba338a838fd3bfb
Source dataset
uspto-grants-1988_03
Patent number
US04732978

Reaction notes

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