2-(o-Tolyl)acetonitrile → Ethyl 5-cyano-4-oxo-5-(2-methylphenyl)pentanoate

HRID 1833837

Reaktionsgleichung

Reaktionsgleichung von HRID 1833837
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:2][CH2:3][C:4]([O:6]CC)=O.[CH3:13][C:14]1[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=1[CH2:16][C:17]#[N:18].[Na]>CO>[C:17]([CH:16]([C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[CH3:13])[C:4](=[O:6])[CH2:3][CH2:2][C:1]([O:10][CH2:11][CH3:12])=[O:9])#[N:18]

Komponenten

5

Edukt 3

HCID 311552-(o-Tolyl)acetonitrileHCID 31249Diethyl SuccinateHCID 5360545Sodium

Produkt 1

HCID 21387700Ethyl 5-cyano-4-oxo-5-(2-methylphenyl)pentanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Diethyl succinate (510 g.) and 2-methylbenzyl cyanide [prepared according to the method of Meisenheimer et al, Ann. 468, 217 (1929); 155 g.] were added to a solution of sodium (42 g.) in dry methanol (585 ml.) at ambient temperature. The mixture was heated under reflux, with stirring, for 16 hours and excess methanol was then removed by distillation under reduced pressure. The residue was dissolved in a mixture of toluene (500 ml.) and water (2000 ml.). The aqueous layer was separated, acidified with concentrated sulphuric acid (50 ml.) and extracted with diethyl ether (3 × 800 ml.). The ethereal extract was washed with water, dried over sodium sulphate and evaporated to dryness to give ethyl 5-cyano-4-oxo-5-(2-methylphenyl)pentanoate (305 g.) in the form of a dark coloured oil.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. customexcess methanol was then removed by distillation under reduced pressure
  4. dissolutionThe residue was dissolved in a mixture of toluene (500 ml.) and water (2000 ml.)
  5. customThe aqueous layer was separated
  6. extractionextracted with diethyl ether (3 × 800 ml.)
  7. extractionThe ethereal extract
  8. washwas washed with water
  9. dry with materialdried over sodium sulphate
  10. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-59529a2ab94b43a7a2fa6076afc0ca13
Quelldatensatz
uspto-grants-1978_01
Patentnummer
US04067723

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