2-Methoxybenzaldehyde → HCID 54423307, Verbindung

HRID 1383438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383438
C([Li])CCC.[Cl-].[CH3:7][S:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:29][O:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=O>O1CCCC1>[CH3:29][O:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=[CH:7][S:8][CH3:9]

Komponenten

5

Edukt 3

HCID 86582-MethoxybenzaldehydeHCID 3083732[(Methylsulfanyl)methyl](triphenyl)phosphanium chlorideHCID 178418339Butyllithium

Produkt 1

HCID 54423307HCID 54423307, VerbindungAusbeute 729,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

2.6 ml of a 1.6 M butyllithium solution in tetrahydrofuran are slowly added dropwise at 0° C. to a solution of 1.5 g of methylmercaptomethyl-triphenyl-phosphonium chloride in anhydrous tetrahydrofuran. After 1 hour, 5.7 g of 2-methoxybenzaldehyde in 50 ml of tetrahydrofuran are added and the resulting mixture is stirred for a further 12 hours at ambient temperature. The solvent is distilled off in vacuo and the residue remaining is taken up in diethylether. After extraction with dilute, aqueous HCl solution, aqueous Na2CO3 solution (17%) and washing with water, the collected organic phases are dried and the solvent is distilled off in vacuo. Chromatography on silica gel (cyclohexane:ethyl acetate 90:10) yields 5.5 g of 1-methoxy-2-(2-methylsulphanyl-vinyl)-benzene.

Aufarbeitung

  1. distillationThe solvent is distilled off in vacuo
  2. extractionAfter extraction
  3. additionwith dilute
  4. washaqueous HCl solution, aqueous Na2CO3 solution (17%) and washing with water
  5. customthe collected organic phases are dried
  6. distillationthe solvent is distilled off in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-236008df97d24241b329fa892340c4fc
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255327B1

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