Quinoline → cis-2,5-Dimethyl-3-hexene-2,5-diol

HRID 1389569

Reaktionsgleichung

Reaktionsgleichung von HRID 1389569
C(=O)([O-])[O-].[Ca+2].N1C2C(=CC=CC=2)C=CC=1.[CH3:16][C:17]([OH:25])([C:19]#[C:20][C:21]([CH3:24])([OH:23])[CH3:22])[CH3:18].[H][H]>CO>[CH3:16][C:17]([OH:25])(/[CH:19]=[CH:20]\[C:21]([CH3:24])([OH:23])[CH3:22])[CH3:18]

Komponenten

6

Edukt 4

HCID 7047QuinolineHCID 88832,5-Dimethyl-3-hexyne-2,5-diolHCID 10112Calcium CarbonateHCID 178418361HCID 178418361, Verbindung2×

Produkt 1

HCID 11126394cis-2,5-Dimethyl-3-hexene-2,5-diolAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.6 g of 5% palladized calcium carbonate and 0.6 g of quinoline were added to a solution of 24 g of 2,5-dimethyl-hex-3-yne-2,5-diol [Ray et al, Am. Soc., Vol. 74 (1952), p. 1247] in 200 ml of methanol and the mixture was stirred with hydrogen until hydrogen absorption ceased. The catalyst was removed by filtration and the filtrate was evaporated to dryness under reduced pressure to obtain 24.2 g of cis 2,5-dimethyl-hex-3-ene-2,5-diol melting at 64° C. which was used as is for the next step.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-468207694ddc487b9aaf2731a4d3a4d5
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04245112

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