18-Crown-6 → 1-(2-Methoxyethenyl)-4-(octyloxy)benzene

HRID 128779

Reaktionsgleichung

Reaktionsgleichung von HRID 128779
CC(C)([O-])C.[K+].[Cl-].[CH3:8][O:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1.[CH2:48]([O:56][C:57]1[CH:64]=[CH:63][C:60]([CH:61]=O)=[CH:59][CH:58]=1)[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]>C1COCC1.CCCCCC>[CH3:8][O:9][CH:10]=[CH:61][C:60]1[CH:63]=[CH:64][C:57]([O:56][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:58][CH:59]=1

Komponenten

7

Edukt 4

HCID 2855718-Crown-6HCID 90358p-(Octyloxy)benzaldehydeHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 537755121-(2-Methoxyethenyl)-4-(octyloxy)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

Potassium t-butoxide (1.9 g) is added to a slurry of methoxymethyl triphenylphosphonium chloride (6.17 g) and 18-Crown-6 (100 mg) in dry THF (40 ml). The mixture is stirred for 5 min, cooled to 15°, and a solution of 4-octyloxybenzaldehyde (3.52 g) in THF (5 ml) is added dropwise. The reaction mixture is stirred at room temperature for 20 min, diluted with 250 ml hexane, and the resulting mixture filtered through a pad of diatomaceous earth. Evaporation of the filtrate leaves crude 1-(2-methoxyethenyl)-4-(octyloxy)benzene as a mixture of cis and trans isomers, containing about 15 mol % triphenylphosphine oxide. The crude material may be used as is, or may be chromatographed with 1:1 hexanedichloromethane.

Aufarbeitung

  1. temperaturecooled to 15°
  2. stirringThe reaction mixture is stirred at room temperature for 20 min
  3. filtrationthe resulting mixture filtered through a pad of diatomaceous earth
  4. customEvaporation of the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-342bcfb170dd446095d890ba2b2078d3
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464865

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