Hydrogen Bromide → 4-Hydroxy-4'-nitrobenzophenone

HRID 634789Notes

Reaction equation

HRID 634789 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 110968174-Hydroxy-4'-nitrobenzophenoneYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d84547fca09548c4968146ed157ca4fd
Source dataset
uspto-grants-2001_02
Patent number
US06184242B2

Reaction notes

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