Acetic Acid → Methyl 2-cyano-3-methylcrotonate

HRID 2305822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305822
[CH3:1][C:2]([CH3:4])=O.[C:5]([CH2:7][C:8]([O:10][CH3:11])=[O:9])#[N:6].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1C=CC=CC=1.O>[C:5]([C:7](=[C:2]([CH3:4])[CH3:1])[C:8]([O:10][CH3:11])=[O:9])#[N:6]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 180AcetoneHCID 7747Methyl cyanoacetateHCID 517165Ammonium Acetate

Produkt 1

HCID 248907Methyl 2-cyano-3-methylcrotonateAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

87 g (1.5 mol) of acetone were initially charged in 100 ml of benzene. After addition of 131 g (1.33 mol) of methyl cyanoacetate, 16 g (0.28 mol) of acetic acid and 9.7 g (0.13 mol) of ammonium acetate, the mixture was heated at reflux on a water separator for 10 hours. For work-up, the mixture was washed twice with ¼-concentrated hydrochloric acid and water. The solution was dried with magnesium sulfate and the solvent was removed, and the resulting crude product was distilled. 108 g (55% yield) of methyl 2-cyano-3-methyl-but-2-enoate were isolated (B.p. 95° C./5.2 mbar).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. washFor work-up, the mixture was washed twice with ¼-concentrated hydrochloric acid and water
  3. dry with materialThe solution was dried with magnesium sulfate
  4. customthe solvent was removed
  5. distillationthe resulting crude product was distilled

Quellen und Nachweise

ORD-Eintrag
ord-ae9795f43f664da7b6fe6b9e66e97815
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06441044B1

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