Hydrochloric Acid → 8-(4-(Trifluoromethoxy)-phenoxy)-1-octanol

HRID 36138Notes

Reaction equation

HRID 36138 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22].C([O-])([O-])=O.[K+].[K+].Cl>CN(C)C=O>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][OH:22])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 70015p-(Trifluoromethoxy)phenolHCID 1626071-Octanol, 8-bromo-

Product 1

HCID 224079298-(4-(Trifluoromethoxy)-phenoxy)-1-octanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5.0 g of 4-(trifluoromethoxy)phenol, 5.87 g of 8-bromo-1-octanol, and 7.76 g of K2CO3 in 56 ml of anhydrous dimethylformamide is stirred and heated at 80° C. for 16 hours. The reaction mixture is poured into dilute HCl solution and the mixture is extracted three times with ethyl acetate. The combined extracts are washed with brine and dried over MgSO4. After filtration and concentration, the crude product is purified by flash chromatography on silica gel, eluting with a 4:1 hexane/ethyl acetate mixture to give the title compound 8-(4-(trifluoromethoxy)-phenoxy)-1-octanol.

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration and concentration
  5. customthe crude product is purified by flash chromatography on silica gel
  6. washeluting with a 4:1 hexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-a10137d50be249069508be380a70b375
Source dataset
uspto-grants-1995_05
Patent number
US05412137

Reaction notes

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