Monobenzone → 1-(Benzyloxy)-4-(4,4,4-trifluorobutoxy)benzene

HRID 511717Notes

Reaction equation

HRID 511717 reaction equation
I[CH2:2][CH2:3][CH2:4][C:5]([F:8])([F:7])[F:6].[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN1C(=O)CCC1>[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:2][CH2:3][CH2:4][C:5]([F:8])([F:7])[F:6])=[CH:21][CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 7638MonobenzoneHCID 11430Potassium CarbonateHCID 27751891,1,1-Trifluoro-4-iodobutane

Product 1

HCID 674558991-(Benzyloxy)-4-(4,4,4-trifluorobutoxy)benzene

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

464.5 g (1.95 mol) of 4-iodo-1,1,1-trifluorobutane, 390.4 g (1.95 mol) of 4-(benzyloxy)phenol and 539.5 g (3.90 mol) of potassium carbonate are dissolved in 3 L of NMP. The mixture is heated to 80° C. overnight. The solution is cooled to room temperature and the reaction mixture is extracted with ethyl acetate and water. The organic phase is washed repeatedly with water, dried over sodium sulfate, filtrated and concentrated under reduced pressure to give 580 g of

Workup

  1. temperatureThe solution is cooled to room temperature
  2. extractionthe reaction mixture is extracted with ethyl acetate and water
  3. washThe organic phase is washed repeatedly with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. customto give 580 g of

Sources & evidence

ORD record
ord-cb97ab61a24c45898f59e4681835123c
Source dataset
uspto-grants-2015_08
Patent number
US09097938B2

Reaction notes

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