Methyl Ethyl Ketone → 2,3-Difluoro-4'-(11-hydroxyundecyl)oxybiphenyl

HRID 1289376

Reaktionsgleichung

Reaktionsgleichung von HRID 1289376
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28].C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 7416311-Bromo-1-undecanolHCID 189208344-(2,3-Difluorophenyl)phenol

Produkt 1

HCID 189208442,3-Difluoro-4'-(11-hydroxyundecyl)oxybiphenylAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

First, 5.0 g of 2,3-difluoro-4'-hydroxybiphenyl, 7.3 g of 11-bromo-1-undecanol, 6.7 g of potassium carbonate, and 150 ml of methyl ethyl ketone were placed in a 200 ml flask. 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 8 g of 2,3-difluoro-4'-(11-hydroxyundecyl)oxybiphenyl (Y: 88%). The compound thus obtained had a purity of 98.8% by GC.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c026200e6b20460c83d86db29ad9d85a
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750213

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