Propargyl alcohol → HCID 19736363, Verbindung

HRID 326217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 326217
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[CH2:10][CH2:11][C:12](=[O:14])[CH3:13].[CH2:15]([OH:18])[C:16]#[CH:17].[OH-].[K+].[NH4+].[Cl-]>C1COCC1.O>[CH3:13][C:12]([OH:14])([CH2:11][CH2:10][C:3]1[C:4]([CH3:8])([CH3:9])[CH2:5][CH2:6][CH2:7][C:2]=1[CH3:1])[C:17]#[C:16][CH2:15][OH:18]

Komponenten

7

Edukt 4

HCID 7859Propargyl alcoholHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 519382Dihydro-beta-ionone

Produkt 1

HCID 19736363HCID 19736363, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butanone (107 g, 0.55 mol) and propargyl alcohol (34 g, 0.61 mol) was added dropwise during 1.5 h to a mechanically stirred slurry of powered KOH (Fluka, 230 g, 4.1 mol) in THF (tetrahydrofuran 800 ml) maintained at 20° C. After a further 3 h, the brown mixture was poured into a cold solution of NH4Cl (250 g, 4.7 mol) in H2O (800 ml) and the phases separated. Extraction of the aqueous phase with ether and concentration of the combined organic phase afforded a reddish brown solid which was recrystallized from petroleum ether (80/100) to furnish 4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-hexyn-1,4-diol as a pale yellow powder (110 g, 80% yield).

Aufarbeitung

  1. customthe phases separated
  2. extractionExtraction of the aqueous phase with ether and concentration of the combined organic phase
  3. customafforded a reddish brown solid which
  4. customwas recrystallized from petroleum ether (80/100)

Quellen und Nachweise

ORD-Eintrag
ord-00d63733f46d46a6b7d1b2e0815978e9
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05268355

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