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Water → 2-(2-(2-(2-Hydroxyethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

HRID 1199308
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1199308
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].N1C=CC=CC=1.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.O>C(Cl)Cl>[S:26]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 8200Tetraethylene Glycol

Produkt 1

HCID 134560942-(2-(2-(2-Hydroxyethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

A cold (0°) solution of 23.3 g of tetraethylene glycol and 19 g of pyridine in 100 ml of methylene chloride, is treated portionwise while stirring vigorously with a total of 19 g of p-toluenesulphonyl chloride. After completion of the addition the mixture is stirred at room temperature for a further 5 hours. 200 ml of methylene chloride and 100 ml of water are then added thereto and the organic phase is separated. The organic phase is washed successively with 100 ml of 2N hydrochloric acid, 100 ml of 5% sodium hydrogen carbonate solution and 100 ml of water and dried over sodium sulphate. The solvent is removed in a vacuum and the residue is chromatographed over 400 g of silica gel with methylene chloride-ethyl acetate-methanol (5:4:1) as the eluent. In addition to small amounts of tetraethylene glycol ditosylate there are isolated 17 g of tetraethylene glycol monotosylate as a colourless liquid. RF (silica gel/methylene chloride-ethyl acetate-methanol 5:4:1): 0.6.

Aufarbeitung

  1. additionAfter completion of the addition the mixture
  2. customthe organic phase is separated
  3. washThe organic phase is washed successively with 100 ml of 2N hydrochloric acid, 100 ml of 5% sodium hydrogen carbonate solution and 100 ml of water
  4. dry with materialdried over sodium sulphate
  5. customThe solvent is removed in a vacuum
  6. customthe residue is chromatographed over 400 g of silica gel with methylene chloride-ethyl acetate-methanol (5:4:1) as the eluent
  7. additionIn addition to small amounts of tetraethylene glycol ditosylate

Quellen und Nachweise

ORD-Eintrag
ord-f5bfd9d430aa4b5d9ffaef5a6366e337
Quelldatensatz
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04900478

Notizen zur Reaktion

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