Sodium Hydroxide → 2-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-phenoxybenzyl ether

HRID 483748Notes

Reaction equation

HRID 483748 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][CH:7]=1)[CH2:4][OH:5].[O:17]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]([F:15])([F:16])[CH:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[CH:8][CH:7]=1)[CH2:4][O:5][CH2:27][C:26]1[CH:29]=[CH:30][CH:31]=[C:24]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:25]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 10681171(RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-ol

Product 1

HCID 106695812-(4-Ethoxyphenyl)-3,3,3-trifluoropropyl 3-phenoxybenzyl etherYield 29.5%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

A mixture of (RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)propan-3-ol (0.4 g), 3-phenoxybenzyl bromide (0.45 g), tetra-n-butyl-ammonium hydrogen sulphate (0.05 g) and aqueous sodium hydroxide solution (40% w/v, 5.0 cm3) was stirred at the ambient temperature for 6 hours after which it was partitioned between water and diethyl ether. The ethereal phase was separated, washed twice with water, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent under reduced pressure. The residual oil (0.75 g) was purified by chromatography on a silica gel column eluted with a mixture of hexane (23 parts by volume) and ethyl acetate (2 parts by volume) to yield (RS)-1,1,1-trifluoro-2-(4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propane (0.21 g) as a viscous oil.

Workup

  1. customwas partitioned between water and diethyl ether
  2. customThe ethereal phase was separated
  3. washwashed twice with water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. concentrationconcentrated by evaporation of the solvent under reduced pressure
  6. customThe residual oil (0.75 g) was purified by chromatography on a silica gel column
  7. washeluted with a mixture of hexane (23 parts by volume) and ethyl acetate (2 parts by volume)

Sources & evidence

ORD record
ord-2e19b0747f2444b1a17a36c25af5d120
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

Loading…