Pyridine → 2-Oxo-2-(4-trifluoromethylphenyl)ethyl phenyl carbonate

HRID 395669

Reaktionsgleichung

Reaktionsgleichung von HRID 395669
[OH:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=[O:4].N1C=CC=CC=1.[C:21](Cl)(=[O:29])[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[C:21](=[O:29])([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:1][CH2:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 112871692-Hydroxy-1-[4-(trifluoromethyl)phenyl]ethan-1-one

Produkt 1

HCID 129929622-Oxo-2-(4-trifluoromethylphenyl)ethyl phenyl carbonateAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 2-hydroxy-4′-trifluoromethyl acetophenone (24.0 g), pyridine (10.3 g) and tetrahydrofuran (200 ml) was added dropwise phenyl chlorocarbonate (20.4 g) under ice-cooling, which was stirred at room temperature for 1 hour. The reaction mixture was concentrated, which was poured into water (500 ml), and extracted with ethyl acetate (150 ml×2). The organic layer was washed with water and then a saturated aqueous solution of sodium chloride, which was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to crystallization by addition of isopropyl ether (100 ml) to give crystals of 2-oxo-2-(4-trifluoromethylphenyl)ethyl phenyl carbonate (18.9 g, 53%). Melting point 134-135° C.

Aufarbeitung

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. additionwhich was poured into water (500 ml)
  4. extractionextracted with ethyl acetate (150 ml×2)
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, which was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue was subjected to crystallization by addition of isopropyl ether (100 ml)

Quellen und Nachweise

ORD-Eintrag
ord-e1d0f28c574a4582986d3542d7789975
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605629B1

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