1-Butanol → Acetamide, N-[2-(4-hydroxyphenyl)-1-methylethyl]-

HRID 441574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 441574
C([O:4][C:5]1[CH:17]=[CH:16][C:8]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].O.C(O)CCC>C(OCC)(=O)C>[OH:4][C:5]1[CH:17]=[CH:16][C:8]([CH2:9][CH:10]([NH:12][C:13](=[O:15])[CH3:14])[CH3:11])=[CH:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 2631-ButanolHCID 962WaterHCID 14798Sodium Hydroxide2×HCID 520328N,O-Diacetyl-4-hydroxyamphetamine

Produkt 1

HCID 584229Acetamide, N-[2-(4-hydroxyphenyl)-1-methylethyl]-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A 0.2 mole preparation of rac. N-(4-acetoxy-alpha-methylphenethyl)acetamide was prepared as described above except that a more concentrated sodium hydroxide solution was used: i.e., 16 g. of NaOH in 50 ml. of water. Overnight, the oil partially crystallized. The mixture was warmed to 60°-70° C. and 110 ml. of 10% NaOH solution added in portions until a permanent pH of 9 was obtained. The mixture was cooled to 25° C., 125 ml. of n-butanol was added; the two phase mixture transferred to a separatory funnel, and the layers separated. Three more extractions with n-butanol were made and the combined extracts dried with anhydrous MgSO4. After removal of the drying agent by filtration, the solvent was distilled in a rotary evaporator. The traces of n-butanol that remained were removed by the addition of 100 ml. of water and reevaporation in a rotary evaporator, whereupon the residue crystallized on cooling; yield 46 g. The product was recrystallized from 450 ml. of boiling water and 26 g. of crystalline material, m.p. 154.4°-158.5° was obtained. An analytical sample was obtained by recrystallization from hot ethyl acetate, m.p. 160.5°-163.5°.

Aufarbeitung

  1. customwas prepared
  2. customOvernight, the oil partially crystallized
  3. temperatureThe mixture was warmed to 60°-70° C.
  4. additionof 10% NaOH solution added in portions until a permanent pH of 9
  5. customwas obtained
  6. customthe two phase mixture transferred to a separatory funnel
  7. customthe layers separated
  8. extractionThree more extractions with n-butanol
  9. dry with materialthe combined extracts dried with anhydrous MgSO4
  10. customAfter removal of the drying agent
  11. filtrationby filtration
  12. distillationthe solvent was distilled in a rotary evaporator
  13. customThe traces of n-butanol that remained were removed by the addition of 100 ml
  14. customof water and reevaporation
  15. customin a rotary evaporator
  16. customwhereupon the residue crystallized
  17. temperatureon cooling
  18. customThe product was recrystallized from 450 ml
  19. customof crystalline material, m.p. 154.4°-158.5° was obtained

Quellen und Nachweise

ORD-Eintrag
ord-d451be26a12c43aaadf94a8f259fcf38
Quelldatensatz
uspto-grants-1977_08
Patentnummer
US04041076

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