Toluene → Ethyl 2-[4-(2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate

HRID 747585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747585
[I-].[Na+].Cl[Si](C)(C)C.O[CH:9]([C:15]1[C:27]([CH3:28])=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]([CH3:29])[CH:16]=1)[CH:10]([O:13][CH3:14])[O:11][CH3:12].C1(C)C=CC=CC=1>C(#N)C.N1C=CC=CC=1>[CH3:12][O:11][CH:10]([O:13][CH3:14])[CH2:9][C:15]1[C:27]([CH3:28])=[CH:26][C:18]([O:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:17]([CH3:29])[CH:16]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 10470761Ethyl 2-[4-(1-hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate

Produkt 1

HCID 9971795Ethyl 2-[4-(2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetateAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of sodium iodide (72 g) and chlorotrimethylsilane (52 g) in acetonitrile (180 g) was added dropwise a solution of ethyl 2-[4-(1-hydroxy-2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate (50 g) in acetonitrile (80 g) in an ice-salt bath. The mixture was stirred for 30 minutes, and then toluene (400 g) and pyridine (25 g) were added. The reaction mixture was washed with an aqueous solution of sodium thiosulfate, an aqueous solution of citric acid, an aqueous solution of sodium bicarbonate and brine successively. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give ethyl 2-[4-(2,2-dimethoxyethyl)-2,5-dimethylphenoxy]acetate (43 g).

Aufarbeitung

  1. washThe reaction mixture was washed with an aqueous solution of sodium thiosulfate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-dbfbf843dd53437f9d9a7d157743b924
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396954B2

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