Benzyl Chloride → 1-Phenyl-2,5,8,11-tetraoxatridecan-13-ol

HRID 6638

Reaktionsgleichung

Reaktionsgleichung von HRID 6638
[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].[OH-].[Na+].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[Na+].[Cl-]>[CH2:16]([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:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 8200Tetraethylene GlycolHCID 14798Sodium Hydroxide

Produkt 1

HCID 110769571-Phenyl-2,5,8,11-tetraoxatridecan-13-olAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5234Sodium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the oil of non-polydispersed tetraethylene glycol (19.4 g, 0.10 mol) was added a solution of NaOH (4.0 g in 4.0 mL) and the reaction was stirred for 15 mm. Then benzyl chloride (3.54 mL, 30.8 mmol) was added and the reaction mixture was heated to 100° C. and stirred overnight. The reaction mixture was cooled to room temperature, diluted with sat. NaCl (250 mL), and washed CH2Cl2 (2×200 mL). The organic layers were combined, washed sat. NaCl, dried MgSO4, and chromatographed (silica, ethyl acetate) to afford the non-polydispersed title compound as a yellow oil (6.21 g, 71% yield).

Aufarbeitung

  1. stirringstirred overnight
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed CH2Cl2 (2×200 mL)
  4. washwashed sat. NaCl, dried MgSO4
  5. customchromatographed (silica, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c57b5f4f796a498980b66acdd117c019
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084121B2

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