Benzoate → 3-Fluoro-4-(1,1,1-trifluoro-2-octyloxycarbonyl)phenyl 4-octyloxybiphenyl-4'-carboxylate

HRID 1728523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728523
C([O-])(=O)C1C=CC=CC=1.[F:10][C:11]1[CH:30]=[C:29]([OH:31])[CH:28]=[CH:27][C:12]=1[C:13]([O:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:17]([F:20])([F:19])[F:18])=[O:14].CN(C1C=CC=CN=1)C.[CH2:41]([O:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][C:59]([C:62](Cl)=[O:63])=[CH:58][CH:57]=2)=[CH:52][CH:51]=1)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>C(Cl)Cl.O.C(N(CC)CC)C>[CH2:41]([O:49][C:50]1[CH:55]=[CH:54][C:53]([C:56]2[CH:61]=[CH:60][C:59]([C:62]([O:31][C:29]3[CH:28]=[CH:27][C:12]([C:13]([O:15][CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:17]([F:19])([F:20])[F:18])=[O:14])=[C:11]([F:10])[CH:30]=3)=[O:63])=[CH:58][CH:57]=2)=[CH:52][CH:51]=1)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Komponenten

8

Edukt 4

HCID 242BenzoateHCID 218852-DimethylaminopyridineHCID 110784734-(4-Octyloxyphenyl)benzoyl chlorideHCID 199208191,1,1-Trifluorooctan-2-YL 2-fluoro-4-hydroxybenzoate

Produkt 1

HCID 537499373-Fluoro-4-(1,1,1-trifluoro-2-octyloxycarbonyl)phenyl 4-octyloxybiphenyl-4'-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of the benzoate (1.6 g) obtained in (1) above, triethylamine (0.5 g) and dimethylaminopyridine (0.5 g) in methylene chloride (10 ml) was slowly added under cooling a solution of 4-n-octyloxybiphenyl-4'-carboxylic acid chloride (1.7 g) in methylene chloride (10 ml). The mixture was left to stand until it reached room temperature and stirred overnight. The mixture was poured in water and extracted with methylene chloride. The extracted layer was washed with dilute aqueous hydrochloric acid solution, water, 1N aqueous sodium carbonate solution and water, in this order, and dehydrated over anhydrous magnesium sulfate. After the solution was distilled under reduced pressure to remove the solvent, the residue was purified by silica-gel column chromatography and recrystallized from anhydrous ethanol to obtain the titled compound (0.8 g, [α]D20 =+25.6°). ##STR62##

Aufarbeitung

  1. waitThe mixture was left
  2. customreached room temperature
  3. extractionextracted with methylene chloride
  4. washThe extracted layer was washed with dilute aqueous hydrochloric acid solution, water, 1N aqueous sodium carbonate solution and water, in this order
  5. distillationAfter the solution was distilled under reduced pressure
  6. customto remove the solvent
  7. customthe residue was purified by silica-gel column chromatography
  8. customrecrystallized from anhydrous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-1390450551ed46a9ad1943b31e2863f6
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05328641

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