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

HRID 654073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654073
[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-cyano-phenol 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-b591801eab71441b9a149272edd4de53
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05130314

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