Monobenzone → 1-(Benzyloxy)-4-(2,2,2-trifluoroethoxy)benzene

HRID 1420812Notes

Reaction equation

HRID 1420812 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:16][C:17]([F:31])([F:30])[CH2:18]OS(C1C=CC(C)=CC=1)(=O)=O.[H-].[Na+]>CN(C)C=O.O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:18][C:17]([F:31])([F:30])[F:16])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

Product 1

HCID 227373741-(Benzyloxy)-4-(2,2,2-trifluoroethoxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-benzyloxyphenol (5 g) and 2,2,2-trifluoroethyl-p-toluenesulphonate (5 g) in dimethylformamide (50 ml) was added sodium hydride (60% dispersion in oil, 2.3 g) and the solution heated to 110° C. for 16 h. The mixture was cooled, diluted with water and the product extracted into ethyl acetate. The organic phase was washed with water, brine and dried (MgSO4). The solvent was remove in vacuo and the residue chromatographed on silica gel (eluting with 10% diethyl ether/hexane) to give the the title compound as a solid, m.p. 72-74° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe product extracted into ethyl acetate
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was remove in vacuo
  6. customthe residue chromatographed on silica gel (eluting with 10% diethyl ether/hexane)

Sources & evidence

ORD record
ord-af8570c164c4467abd0e360fc35308d0
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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