Sodium Hydroxide → (2S)-(+)-(5-chloro-2-cyanophenoxy)-2,3-epoxypropane

HRID 1090625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1090625
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[C:6]([OH:8])[CH:7]=1.[CH2:11]1[O:13][C@H:12]1[CH2:14]Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[C:6]([CH:7]=1)[O:8][CH2:14][C@H:12]1[O:13][CH2:11]1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 2734062(-)-EpichlorohydrinHCID 34427894-Chloro-2-hydroxybenzonitrile

Produkt 1

HCID 10774787(2S)-(+)-(5-chloro-2-cyanophenoxy)-2,3-epoxypropaneAusbeute 35,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixed solution of 5.0 g of 5-chloro-2-cyanophenol and 6.0 g of R-(-)-epichlorohydrin was heated at 120° C. for 2 hours under a nitrogen stream. Toluene (50 ml), 0.1 g of benzyl triethylammonium chloride and 20 ml of a 30% sodium hydroxide were added, and the mixture was stirred at room temperature for 2 hours. The organic layer was separated and dried over magnesium sulfate. The solvent was then evaporated. Ethanol was added to the residue to crystallize it. The crystals were then recrystrallized from ethyl acetate to give 2.4 g (2S)-(+)-(5-chloro-2-cyanophenoxy)-2,3-epoxypropane.

Aufarbeitung

  1. customThe organic layer was separated
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was then evaporated
  4. additionEthanol was added to the residue
  5. customto crystallize it

Quellen und Nachweise

ORD-Eintrag
ord-b7a0b7af2c03418e8dc3d2b1ab44eb04
Quelldatensatz
uspto-grants-1992_01
Patentnummer
US05082844

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