Diethyl Ether → 4-Benzyloxybenzotrifluoride

HRID 269550Notes

Reaction equation

HRID 269550 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CC(C)=O.O>[CH2:12]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenol

Product 1

HCID 27981684-Benzyloxybenzotrifluoride

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 4-hydroxybenzotrifluoride (8.55 g, 52.78 mmol) in acetone (200 ml) was treated with benzyl bromide (9.87 g, 6.86 ml, 58.05 mmol) and potassium carbonate (10.94 g, 79.16 mmol). The mixture was stirred and heated to reflux under nitrogen for 3 h. After cooling, diethyl ether (400 ml) and water (400 ml) were added and the aqueous phase re-extracted with diethyl ether (100 ml). The combined organic layers were washed with water, dried (MgSO4) and the solvent removed in vacuo to leave the title compound as a white solid. (12.71 g, 95%)

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 3 h
  3. temperatureAfter cooling
  4. extractionthe aqueous phase re-extracted with diethyl ether (100 ml)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-81ae0fc634cb473dbd06177920facf11
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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