Toluene → N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2-tetradecylsuccinimide

HRID 2372868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2372868
[CH2:1]([CH:15]1[CH2:20][C:19](=[O:21])[O:18][C:16]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:22]([C:26]1[CH:27]=[C:28]([CH2:37][CH2:38][C:39]([NH:41][NH2:42])=[O:40])[CH:29]=[C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:31]=1[OH:32])([CH3:25])([CH3:24])[CH3:23].C1(C)C=CC=CC=1>O>[C:33]([C:30]1[CH:29]=[C:28]([CH2:37][CH2:38][C:39]([NH:41][N:42]2[C:19](=[O:21])[CH2:20][CH:15]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:16]2=[O:18])=[O:40])[CH:27]=[C:26]([C:22]([CH3:23])([CH3:24])[CH3:25])[C:31]=1[OH:32])([CH3:34])([CH3:35])[CH3:36]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazideHCID 98128Dihydro-3-tetradecylfuran-2,5-dione

Produkt 1

HCID 15044332N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-2-tetradecylsuccinimideAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 2-tetradecylsuccinic anhydride (17.2 g, 52.5 mmol), 3-(3,5-di-t-butyl-4-hydroxyphenyl)propanoic acid hydrazide (15.4 g, 52.5 mmol) and 40 ml of toluene was refluxed for about one hour under a nitrogen atmosphere with the azeotropic removal of water. The bulk of the solvent was then allowed to distill off. Residual solvent was removed by placing the heated mixture (140° C.) under vacuum for 15 minutes. The bath used to heat the mixture was cooled to 70° C. and the vacuum was released. The resulting viscous melt was dissolved in 120 ml of acetone and suction filtered to remove mechanical impurities. The filtrate was diluted to 700 ml with acetone. This solution was cooled in an ice/water bath to precipitate the product which was collected by vacuum filtration. The filtrate was then re-cooled in a -20° C. acetone/dry ice bath to obtain additional product which was also collected by filtration. The collected solids were combined, air dried on a sheet of paper and finally high vacuum dried to give 25.3 g of a white solid having a melting range of 70°-77° C.

Aufarbeitung

  1. distillationto distill off
  2. customResidual solvent was removed
  3. customthe heated mixture (140° C.)
  4. customfor 15 minutes
  5. temperatureto heat the mixture
  6. dissolutionThe resulting viscous melt was dissolved in 120 ml of acetone
  7. filtrationsuction filtered
  8. customto remove mechanical impurities
  9. additionThe filtrate was diluted to 700 ml with acetone
  10. temperatureThis solution was cooled in an ice/water bath
  11. customto precipitate the product which
  12. filtrationwas collected by vacuum filtration
  13. temperatureThe filtrate was then re-cooled in a -20° C. acetone/dry ice bath
  14. customto obtain additional product which
  15. filtrationwas also collected by filtration
  16. customair dried on a sheet of paper and finally high vacuum
  17. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d392845a878a48f5b771af6edc1e89eb
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05100940

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