Chloroform → HCID 54386604, Verbindung

HRID 1196172

Reaktionsgleichung

Reaktionsgleichung von HRID 1196172
[CH3:1][C:2]([CH3:11])=[CH:3][CH2:4][CH2:5][C:6]([OH:10])([C:8]#[CH:9])[CH3:7].[OH-].[Na+].[CH:14]([Cl:17])(Cl)[Cl:15]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:15][C:14]1([Cl:17])[C:2]([CH3:1])([CH3:11])[CH:3]1[CH2:4][CH2:5][C:6]([CH3:7])([OH:10])[C:8]#[CH:9]

Komponenten

5

Edukt 3

HCID 6212Chloroform2×HCID 14798Sodium Hydroxide2×HCID 62842Dehydrolinalool

Produkt 1

HCID 54386604HCID 54386604, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 66133Benzyl triethylammonium chlorideKatalysator2×

Versuchsvorschrift

Dehydrolinalool (400 g, 2.6 mol) and 5.26 g of triethylbenzylammonium chloride are added to a reaction flask. Chloroform (469.6 g, 3.9 mol) is added dropwise. To this solution 223.2 g (2.79 mol) of 50% sodium hydroxide solution are added dropwise within 50 minutes while cooling with ice, whereby the temperature of the reaction mixture rises to 34°. In time the initially viscous mass becomes fluid. After 21 hours of stirring and then again after 37 hours, there are added in each case within 20 minutes while cooling with ice, 160 ml of chloroform, 2.63 g of triethylbenzylammonium chloride and 111.6 g of 50% NaOH. The mixture is stirred at room temperature for a further 60 hours, poured onto ice-water, extracted with methylene chloride, washed neutral, dried over magnesium sulphate and evaporated. In this manner there are obtained 603.7 g (97%) of 5-(2',2'-dichloro-3'3'-dimethylcyclopropyl)-3-methyl-1-pentyn-3-ol.

Aufarbeitung

  1. temperaturewhile cooling with ice, whereby the temperature of the reaction mixture
  2. customrises to 34°
  3. waitagain after 37 hours
  4. additionthere are added in each case within 20 minutes
  5. stirringThe mixture is stirred at room temperature for a further 60 hours
  6. additionpoured onto ice-water
  7. extractionextracted with methylene chloride
  8. washwashed neutral
  9. dry with materialdried over magnesium sulphate
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-88291aa346b440e5b83b5925d1fc6679
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05113021

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