Sodium Cyanide → 3-Hydroxy-3-methylpentanedinitrile

HRID 725756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 725756
[CH3:1][C:2]1([CH2:5]Cl)[CH2:4][O:3]1.[C-:7]#[N:8].[Na+].[C-:10]#[N:11].[K+]>Cl.O>[C:7]([CH2:4][C:2]([CH3:1])([OH:3])[CH2:5][C:10]#[N:11])#[N:8]

Komponenten

6

Edukt 3

HCID 8929Sodium CyanideHCID 9032Potassium CyanideHCID 952202-(Chloromethyl)-2-methyloxirane

Produkt 1

HCID 127207073-Hydroxy-3-methylpentanedinitrileAusbeute 96,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 50 g 2-methyl-2-chloromethyloxirane in 23 ml concentrated hydrochloric acid at ice-bath temperature a solution of 27.4 g sodium cyanide in 23 ml hydrochloric acid was added. After stirring for 10 hours at that temperature the reaction mixture was warmed to 40° C. and a solution of 33.8 g potassium cyanide in 50 ml water was added. The resulting mixture was warmed to 50° C. and stirred for 4 hours. After cooling the solution was neutralized and extracted three times with 150 ml ethyl acetate each. The combined organic layers were dried with anhydrous magnesium sulphate. Removal of the solvent afforded 56.4 g (96%) of 1,3-dicyano-2-methyl-2-hydroxypropane. This crude material was sufficiently pure to be submitted directly to the following ring closure.

Aufarbeitung

  1. temperatureThe resulting mixture was warmed to 50° C.
  2. stirringstirred for 4 hours
  3. temperatureAfter cooling the solution
  4. extractionextracted three times with 150 ml ethyl acetate each
  5. dry with materialThe combined organic layers were dried with anhydrous magnesium sulphate
  6. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-20f1560b8d234f3482d421b75825d032
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05707932

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