Salicyl Alcohol → [2-(4'-Trifluoromethylbiphenyl-4-ylmethoxy)phenyl]methanol

HRID 1672625Notes

Reaction equation

HRID 1672625 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].Cl[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:25][C:24]([F:26])([F:27])[C:21]1[CH:20]=[CH:19][C:18]([C:15]2[CH:16]=[CH:17][C:12]([CH2:11][O:1][C:2]3[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=3[CH2:4][OH:5])=[CH:13][CH:14]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 5146Salicyl AlcoholHCID 11430Potassium CarbonateHCID 114599214-(4-Trifluoromethylphenyl)benzylchloride

Product 1

HCID 57864370[2-(4'-Trifluoromethylbiphenyl-4-ylmethoxy)phenyl]methanolYield 89.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4.59 g (36.94 mmol) of 2-hydroxybenzyl alcohol in 200 ml of dry acetonitrile is mixed with 10 g (36.94 mmol) of 4-chloromethyl-4′-trifluoromethylbiphenyl from Example 23A and 6.13 g (44.33 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The resulting organic phase is concentrated. The crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1). 11.8 g (32.92 mmol, 89% yield) of a solid are obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe resulting organic phase is concentrated
  7. customThe crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record
ord-f156c46a1d504beeb504970a7234d69a
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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