2-Chloro-1,1-diethoxyethane → 3-(2,2-Diethoxyethoxy)-5-chlorophenol

HRID 972119

Reaktionsgleichung

Reaktionsgleichung von HRID 972119
[Na].[OH:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([Cl:9])[CH:8]=1.Cl[CH2:12][CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].[Cl-].[NH4+]>O.CN(C)C=O>[CH2:15]([O:14][CH:13]([O:17][CH2:18][CH3:19])[CH2:12][O:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([Cl:9])[CH:8]=1)[CH3:16]

Komponenten

7

Edukt 4

HCID 121282-Chloro-1,1-diethoxyethaneHCID 25517Ammonium ChlorideHCID 945541,3-Benzenediol, 5-chloro-HCID 5360545Sodium

Produkt 1

HCID 203966933-(2,2-Diethoxyethoxy)-5-chlorophenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

The monosodium salt of 3-hydroxy-5-chlorophenol (0.05 mole) and dimethylformamide (75 ml) are charged under nitrogen gas into a glass reacton vessel equipped with a mechanical stirrer, thermometer and addition funnel. The mixture is stirred until dissolved, and 1-chloro-2,2-diethoxyethane (0.05 mole) is added dropwise over a period of about 20 minutes. After the addition is completed, the reaction mixture is heated at about 90° C. with stirring for a period of about 48 hours. After this time water (200 ml) is added, and the reaction mixture is neutralized with ammonium chloride. The reaction mixture is then extracted with chloroform, and the organic phase is separated from the aqueous phase. The organic phase is then stripped of solvent, leaving an oil. This oil is distilled under reduced pressure to yield the desired product 3-(2,2-diethoxyethoxy)-5-chlorophenol.

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. additionthermometer and addition funnel
  3. dissolutionuntil dissolved
  4. additionAfter the addition
  5. stirringwith stirring for a period of about 48 hours
  6. extractionThe reaction mixture is then extracted with chloroform
  7. customthe organic phase is separated from the aqueous phase
  8. customleaving an oil
  9. distillationThis oil is distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cff4abb0350044009f83411aa805bcc4
Quelldatensatz
uspto-grants-1979_07
Patentnummer
US04163112

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