Ethylene Glycol → HCID 20294078, Verbindung

HRID 596548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 596548
C[C:2]1[C:7](C)=[CH:6][C:5]([CH2:9]C#N)=[C:4]([CH2:12]C#N)[CH:3]=1.[OH2:15].[CH:16]([CH:18]=[O:19])=O.[CH:20]([CH:22]=[O:23])=O.[OH-:24].[K+].[CH2:26](O)[CH2:27]O>CO>[CH3:9][C:5]1[CH:6]=[C:7]2[C:2](=[CH:3][C:4]=1[CH3:12])[C:20]([C:22]([OH:23])=[O:15])=[CH:27][CH:26]=[C:16]2[C:18]([OH:19])=[O:24]

Komponenten

7

Edukt 5

HCID 174Ethylene GlycolHCID 7860GlyoxalHCID 14797Potassium Hydroxide3×HCID 3051422-[2-(Cyanomethyl)-4,5-dimethylphenyl]acetonitrileHCID 21880647Glyoxal hydrate

Produkt 1

HCID 20294078HCID 20294078, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

18.4 parts of 4,5-dimethyl-1,2-bis-cyanomethyl-benzene and 8.4 parts of glyoxal hydrate (trimer) (3C2H2O2.2H2O), containing 80% of glyoxal to be liberated, are stirred in 100 parts by volume of methanol. With stirring and under nitrogen, 11.2 parts of powdered potassium hydroxide are added to the reaction mixture by small amounts at 0° to 5° C. After the addition of potassium hydroxide, stirring is continued for 5 hours at 0° to 5° C under nitrogen. The slightly brown coloured reaction mixture is subsequently diluted with 100 parts by volume of ethylene glycol and then, after addition of 28 parts of potassium hydroxide, heated slowly to 190° C under nitrogen while the methanol is distilled off and ammonia escapes at 80° C. After it has been stirred for 5 hours at 185° to 190° C under nitrogen, the reaction mixture is worked up as described in Example 7 to yield 7.5 parts of 6,7-dimethyl-naphthalene-1,4-dicarboxylic acid (31% of theory) of formula ##STR53## in the form of slightly brown crystalline powder with a melting point of 268°-280° C. Small, pale yellow needles with a melting point of 288°-291° C are obtained after one recrystallisation from glacial acetic acid with activated carbon. The 4,5-dimethyl-1,2-bis-cyanomethyl-benzene used as starting material can be obtained as described in Example 4.

Aufarbeitung

  1. stirringstirring
  2. distillationis distilled off
  3. customat 80° C
  4. stirringAfter it has been stirred for 5 hours at 185° to 190° C under nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-58c8070421124c63a813fcc06cf8151f
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011261

Notizen zur Reaktion

Wird geladen…