Benzocaine → Octadecyl 4-aminobenzoate

HRID 482075

Reaktionsgleichung

Reaktionsgleichung von HRID 482075
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[NH2:20][C:21]1[CH:31]=[CH:30][C:24]([C:25](OCC)=[O:26])=[CH:23][CH:22]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([O:19][C:25](=[O:26])[C:24]1[CH:30]=[CH:31][C:21]([NH2:20])=[CH:22][CH:23]=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][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Komponenten

4

Edukt 3

HCID 2337BenzocaineHCID 6101p-Toluenesulfonic acidHCID 8221Stearyl Alcohol

Produkt 1

HCID 19065294Octadecyl 4-aminobenzoateAusbeute 121,9 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A 1-liter round bottom flask was fitted with a reflux condenser, Dean Stark trap and heating mantle and charged with 54 g (0.20 mole) of 1-octadecanol, 33 g (0.20 mole) ethyl 4-aminobenzoate, 8 g of p-toluenesulfonic acid and 500 ml of mixed xylenes. The flask was flushed with nitrogen and sealed under a nitrogen balloon. The reaction system was heated to reflux with a pot temperature of about 140° C. and allowed to reflux for about 1/2 hour before a 25 ml-aliquot of xylenes-ethanol mixture was removed through the Dean-Stark trap. Every 5-10 minutes, another 25 ml aliquot of the xylenes-ethanol mixture was removed until a total of 400 ml had been withdrawn from the reaction mixture and the pot attained a temperature of 150° C. Remaining volatiles were removed under 29 inches of Hg vacuum at 70° C. in a vacuum oven to give 95 g of an off-white waxy material melting at 60°-70° C., with an infrared spectrum showing the amino-aromatic ester with a long-chain aliphatic tail.

Aufarbeitung

  1. customA 1-liter round bottom flask was fitted with a reflux condenser
  2. temperatureDean Stark trap and heating mantle
  3. customThe flask was flushed with nitrogen
  4. customsealed under a nitrogen balloon
  5. temperatureThe reaction system was heated
  6. temperatureto reflux for about 1/2 hour before a 25 ml-aliquot of xylenes-ethanol mixture
  7. customwas removed through the Dean-Stark trap
  8. customEvery 5-10 minutes, another 25 ml aliquot of the xylenes-ethanol mixture was removed until a total of 400 ml
  9. customhad been withdrawn from the reaction mixture
  10. customa temperature of 150° C
  11. customRemaining volatiles were removed under 29 inches of Hg vacuum at 70° C. in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-60c6dd9094f34651b1958cc8daf9347e
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792800

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