Benzaldehyde → Ccris 2231

HRID 1287417

Reaktionsgleichung

Reaktionsgleichung von HRID 1287417
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1)=[O:3].[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>C(O)C>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH:1]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 74764'-Methoxyacetophenone2×HCID 14798Sodium Hydroxide

Produkt 1

HCID 92853Ccris 2231Ausbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

50.1 g. (0.333 m) 4-methoxyacetophenone and 35.4 g (0.333 m) benzaldehyde were combined in a 500 ml Erlenmeyer flask, with the 4-methoxyacetophenone being previously melted. Then 80 ml 5N NaOH solution (appr.) (1.2 × 0.333 m) was added to the mixture. Approximately 40 ml absolute ethanol was added to the stirred mixture in small portions to keep the mixture homogeneous. It was let stir at room temperature overnight, and a solid white cake resulted. The solid was filtered, washed with water, and then recrystallized from methanol/water to give 72.3 g (91%) of 1-(4-methoxyphenyl)-3-phenyl-2-propen-1-one. 10 g (0.0420 m) of this compound and 160 mg Pd on C (10%) were combined with about 200 ml ethyl acetate and placed under 1 atm of hydrogen. Upon stirring, the mixture absorbed 950 ml H2 (calc. 940 ml) and stopped. The reaction mixture was filtered and the clear solution was concentrated to obtain 9.8 g (98%) of 1-(4-methoxyphenyl)-3-phenyl-1-propanone.

Aufarbeitung

  1. customa solid white cake resulted
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customrecrystallized from methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-7b6aeeb477794a78b89206bf7879b985
Quelldatensatz
uspto-grants-1976_10
Patentnummer
US03984501

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