Methyl Ethyl Ketone → 2,3-Difluoro-4'-(6-hydroxyhexyl)oxybiphenyl

HRID 1289385

Reaction equation

HRID 1289385 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O>[F:9][C:10]1[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 779706-Bromo-1-hexanolHCID 189208344-(2,3-Difluorophenyl)phenol

Product 1

HCID 189208402,3-Difluoro-4'-(6-hydroxyhexyl)oxybiphenylYield 63.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 5 g of 6-bromo-1-hexanol, 5.7 g of 2,3difluoro-4'-hydroxybiphenyl, 7.6 g of potassium carbonate, and 70 ml of methyl ethyl ketone were placed in a 100 ml flask. Then, the mixture was stirred under reflux for 20 hours. The reaction mixture was poured into water, and an organic layer was extracted with toluene. The toluene layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was recrystallized from acetone to obtain 5.4 g of 2,3-difluoro-4'-(6-hydroxyhexyl)oxybiphenyl (Y: 63.5%). The compound thus obtained had a purity of 99.9% by GC.

Workup

  1. temperatureunder reflux for 20 hours
  2. extractionan organic layer was extracted with toluene
  3. washThe toluene layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away
  6. customThe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-be28440a12e4484a887f9ddf837cce26
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Linked notes

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