Methyl Ethyl Ketone → 2,3-Difluoro-4'-(16-hydroxyhexadecyl)oxybiphenyl

HRID 1289393

Reaction equation

HRID 1289393 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18].[F:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=1[C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O>[F:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=1[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:18])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 275701316-Bromo-1-hexadecanolHCID 189208344-(2,3-Difluorophenyl)phenol

Product 1

HCID 189208642,3-Difluoro-4'-(16-hydroxyhexadecyl)oxybiphenylYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 3 g of 16-bromo-1-hexadecanol, 1.9 g of 2,3-difluoro-4'-hydroxybiphenyl, 2.6 g of potassium carbonate, and 50 ml of methyl ethyl ketone were placed in a 100 ml flask. The reaction mixture was stirred under reflux for 32 hours. The reaction mixture was poured into water, and an organic layer was extracted with ether. The ether 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 3.5 g of 2,3-difluoro-4'-(16-hydroxyhexadecyl)oxybiphenyl (Y: 84%). The compound thus obtained had a purity of 97.4% by GC.

Workup

  1. temperatureunder reflux for 32 hours
  2. extractionan organic layer was extracted with ether
  3. washThe ether 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-1ab70646ede1462fa027cbbea7af28e8
Source dataset
uspto-grants-1998_05
Patent number
US05750213

Linked notes

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