Hydrochloric Acid → 1,3-Benzenediacetonitrile, 5-(hydroxymethyl)-alpha1,alpha1,alpha3,alpha3-tetramethyl-

HRID 2107764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2107764
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]([CH3:20])([C:18]#[N:19])[CH3:17])[CH:15]=1)[C:9](OC)=[O:10])([CH3:5])[CH3:4])#[N:2].[BH4-].[Li+].Cl>O1CCCC1>[OH:10][CH2:9][C:8]1[CH:7]=[C:6]([C:3]([CH3:5])([CH3:4])[C:1]#[N:2])[CH:15]=[C:14]([C:16]([CH3:20])([CH3:17])[C:18]#[N:19])[CH:13]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 19349383Methyl 3,5-bis(1-cyano-1-methyl ethyl)benzoate

Produkt 1

HCID 193493981,3-Benzenediacetonitrile, 5-(hydroxymethyl)-alpha1,alpha1,alpha3,alpha3-tetramethyl-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of methyl 3,5-bis(1-cyano-1-methyl ethyl)benzoate (5.6 g), lithium borohydride (0.44 g) and tetrahydrofuran (30 ml) was heated under reflux for 2 h. The mixture was cooled and stirred while 2N aqueous hydrochloric acid was added dropwise until the solution remained acidic, and then the mixture was extracted twice with ethyl acetate. The combined extracts were washed with 1N aqueous potasium bicarbonate solution and then dried and evaporated to dryness under reduced pressure to give 2,2'-(5-hydroxymethyl-1,3-phenylene)di(2-methylpropiononitrile), mp. 151°-153°, which was used without further purification.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. temperatureThe mixture was cooled
  4. additionwas added dropwise until the solution
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washThe combined extracts were washed with 1N aqueous potasium bicarbonate solution
  7. customdried
  8. customevaporated to dryness under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5503992b0efd4a88a6a7b80c78e8bad5
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04935437

Notizen zur Reaktion

Wird geladen…