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Triethylamine → 1-Monofluoro-2-decyl 4-octyloxybiphenyl-4'-carboxylate

HRID 1728521
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1728521
[F:1][CH2:2][CH:3]([OH:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].C(N(CC)CC)C.[CH2:20]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([C:41](Cl)=[O:42])=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C(Cl)Cl.O>[CH2:20]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([C:41]([O:12][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:2][F:1])=[O:42])=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 110784734-(4-Octyloxyphenyl)benzoyl chlorideHCID 146853301-Monofluoro-2-decanol

Produkt 1

HCID 190139291-Monofluoro-2-decyl 4-octyloxybiphenyl-4'-carboxylateAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

To a solution of optically active 1-monofluoro-2-decyl alcohol (0.1 g) and triethylamine (0.06 g) in methylene chloride (10 ml) was slowly added under ice cooling a solution of 4-n-octyloxybiphenyl-4'-carboxylic acid chloride (0.22 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 solution 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, purification was made by silica-gel column chromatography to obtain the titled compound (0.16 g).

Aufarbeitung

  1. waitThe mixture was left
  2. customreached room temperature
  3. extractionextracted with methylene chloride
  4. extractionThe solution extracted layer
  5. washwas washed with dilute aqueous hydrochloric acid solution, water, 1N aqueous sodium carbonate solution and water, in this order
  6. distillationAfter the solution was distilled under reduced pressure
  7. customto remove
  8. customthe solvent, purification

Quellen und Nachweise

ORD-Eintrag
ord-c4023e5f2c2c4dde861b43a740c7f1df
Quelldatensatz
uspto-grants-1994_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05328641

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