Hydrochloric Acid → Ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate

HRID 2058066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2058066
[O-]CC.[Na+].[Cl:5][CH:6]([CH2:16][C:17](Cl)([Cl:19])[Cl:18])[C:7]([CH3:15])([CH3:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].Cl>CN(C)C=O>[Cl:5][CH:6]([CH:16]=[C:17]([Cl:18])[Cl:19])[C:7]([CH3:15])([CH3:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 108412Hexanoic acid, 4,6,6,6-tetrachloro-3,3-dimethyl-, ethyl esterHCID 2723922Sodium ethoxide

Produkt 1

HCID 3042523Ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 2.04 g of sodium ethoxide in 60 ml of dimethylformamide was added to a hot solution (140°) of 3.1 g of ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate in 20 ml of dimethylformamide. The mixture was maintained at 140° for 2 hours, then cooled to 0°, neutralized with dry hydrogen chloride and poured into ice water. The aqueous mixture was extracted with ether, and the extract was washed successively with saturated aqueous sodium bicarbonate and sodium chloride. The washed extract was dried over magnesium sulfate and distilled to give 1.81 g (77% yield) of ethyl 4,6,6-trichloro-3,3-dimethyl-5-hexenoate, b.p. 98°-101°/0.6 mm.

Aufarbeitung

  1. temperatureThe mixture was maintained at 140° for 2 hours
  2. temperaturecooled to 0°
  3. extractionThe aqueous mixture was extracted with ether
  4. washthe extract was washed successively with saturated aqueous sodium bicarbonate and sodium chloride
  5. extractionThe washed extract
  6. dry with materialwas dried over magnesium sulfate
  7. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-c603e7c9ffa74bb9b860c3a210d8396d
Quelldatensatz
uspto-grants-1980_07
Patentnummer
US04214097

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