Thionyl Chloride → 4,4-Dimethyl-2-(4'-chloromethylbiphenyl-2-yl)oxazoline

HRID 743754

Reaktionsgleichung

Reaktionsgleichung von HRID 743754
[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19]O)=[CH:15][CH:14]=2)=[N:3]1.S(Cl)([Cl:24])=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:21])[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[CH:18]=[CH:17][C:16]([CH2:19][Cl:24])=[CH:15][CH:14]=2)=[N:3]1

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 110658764,4-Dimethyl-2-(4'hydroxymethylbiphenyl-2-yl)oxazoline

Produkt 1

HCID 109794774,4-Dimethyl-2-(4'-chloromethylbiphenyl-2-yl)oxazolineAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1.0 g (3.55 mmol) of 4,4-dimethyl-2-(4'-hydroxymethylbiphenyl-2-yl)oxazoline was dissolved in methylene chloride (15 ml). Under cooling with ice, 0.51 g (4.29 mmol) of thionyl chloride was dropwise added thereto, followed by stirring for one hour. The reaction liquid was poured into an aqueous solution of sodium hydrogencarbonate, followed by the extraction with methylene chloride. After washing with water and drying, vacuum concentration was conducted. 1.05 g of the title compound was obtained as a crystal (yield 99%). m.p.; 72°-75° C.

Aufarbeitung

  1. additionwas dropwise added
  2. customThe reaction liquid
  3. extractionfollowed by the extraction with methylene chloride
  4. washAfter washing with water
  5. customdrying
  6. concentrationvacuum concentration

Quellen und Nachweise

ORD-Eintrag
ord-01bb6305206246fd99672bfa1b49aa91
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05557002

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