Hydrogen Bromide → (4-Hydroxyphenyl)(4-nitrophenyl)methanone

HRID 723544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723544
C[O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 3477724-Methoxy-4'-nitrobenzophenone

Produkt 1

HCID 11096817(4-Hydroxyphenyl)(4-nitrophenyl)methanoneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of 4-(4-methoxybenzoyl)-nitrobenzene (150 g, 0.58 mol), glacial acetic acid (500 mL), and hydrobromic acid (48% w/w aqueous solution, 400 mL) was heated under reflux for 16 hours. The reaction mixture was cooled to room temperature and poured onto crushed ice. The crude product as filtered, washed several times with water and dried at about 50° C. under high vacuum. Crystallization from ethyl acetate/hexanes gave 4-(4-hydroxybenzoyl)-nitrobenzene (114 g, 81%), m.p. 190–193° C.; Analysis for C13H9NO4: Calc.: C, 64.20; H, 3.73; N, 5.76; Found: C, 63.95; H, 3.65; N, 5.85; MS m/e (%): 243 (M+; 45).

Aufarbeitung

  1. temperatureunder reflux for 16 hours
  2. additionpoured
  3. customonto crushed ice
  4. filtrationThe crude product as filtered
  5. washwashed several times with water
  6. customdried at about 50° C. under high vacuum
  7. customCrystallization from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4b792cdd1a1348979bb896d88498feb2
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141584B2

Notizen zur Reaktion

Wird geladen…