Hydrochloric Acid → HCID 20294074, Verbindung

HRID 596546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596546
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][C:10]#[N:11])=[C:4]([CH2:12][C:13]#[N:14])[CH:3]=1.O.[CH:16]([CH:18]=O)=O.C(C=O)=O.[OH-].[K+].Cl>CO>[CH3:8][C:7]1[CH:6]=[C:5]2[C:4](=[CH:3][C:2]=1[CH3:1])[C:12]([C:13]#[N:14])=[CH:18][CH:16]=[C:9]2[C:10]#[N:11]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 7860GlyoxalHCID 14797Potassium Hydroxide2×HCID 3051422-[2-(cyanomethyl)-4,5-dimethylphenyl]acetonitrileHCID 21880647Glyoxal hydrate

Produkt 1

HCID 20294074HCID 20294074, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

17 parts of 4,5-dimethyl-1,2-bis-cyanomethyl-benzene and 7.8 parts of glyoxal hydrate (trimer) (3C2H2O2.2H2O) containing 80% of glyoxal to be liberated, are stirred in 100 parts by volume of methanol. The reaction mixture is treated at 0° to 5° C, with stirring and under nitrogen, with 10.5 parts of powdered potassium hydroxide added by small amounts. After the addition of potassium hydroxide, stirring is continued for a further 5 hours at 0° to 5° C under nitrogen. The slightly brown coloured reaction mixture is subsequently neutralised with dilute hydrochloric acid, freed from methanol in vacuo and extracted with methylene chloride. The methylene chloride extract is washed neutral with water, dried over sodium sulphate and concentrated to dryness in vacuo. Yield: 18 parts of a brown oil which is chromatographed over aluminium oxide. Elution with chlorobenzene yields 6.5 parts (34% of theory) of 6,7-dimethyl-1,4-di-cyanonaphthalene of formula ##STR46## in the form of white crystals with a melting point of 212°-220° C. Two recrystallisations from alcohol yield small white needles with a melting point of 225°-227° C. The 4,5-dimethyl-1,2-cyanomethyl-benzene used as starting material can be obtained for example as follows according to the reaction scheme: ##STR47##

Aufarbeitung

  1. additionThe reaction mixture is treated at 0° to 5° C
  2. additionadded by small amounts
  3. extractionextracted with methylene chloride
  4. extractionThe methylene chloride extract
  5. washis washed neutral with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated to dryness in vacuo
  8. customYield: 18 parts of a brown oil which is chromatographed over aluminium oxide
  9. washElution with chlorobenzene

Quellen und Nachweise

ORD-Eintrag
ord-8f9716dd334444af9d64ce6c6e08e709
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011261

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