Hydrogen Peroxide → HCID 9820642, compound

HRID 1839906Notes

Reaction equation

HRID 1839906 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[I:16]I.[N+:18]([O-:21])(O)=[O:19].OO>CO>[OH:1][C:2]1[C:3]([N+:18]([O-:21])=[O:19])=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:14][C:15]=1[I:16]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 807IodineHCID 944Nitric AcidHCID 143474-Hydroxybenzophenone

Product 1

HCID 9820642HCID 9820642, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-hydroxybenzophenone (1.98 g, 10 mmol), iodine (10.15 g, 40 mmol), and concentrated nitric acid (5 mL) in 100 mL methanol was stirred for 72 hours at room temperature. Hydrogen peroxide, 30% (4.1 mL, 40 mmol) was then added, and the solution was stirred for another 15 hours. The solvent and excess iodine was removed in vacuo, and the crude product was crystallized from methanol, yielding the title compound as bright orange crystals (2.80 g, 76%). 1H NMR (400 MHz, CDCl3): δ 11.70 (s, 1H), 8.61 (d, J=2.4 Hz, 1H), 8.57 (d, J=2.4 Hz, 1H), 7.75 (d, J=8.0 Hz, 2H), 7.67 (t, J=7.4 Hz, 1H), 7.55 (appar. t, J=7.6 Hz, 2H). HPLC (40-90), 12.60 min.

Workup

  1. customThe solvent and excess iodine was removed in vacuo
  2. customthe crude product was crystallized from methanol

Sources & evidence

ORD record
ord-9670ffacd9c44c87be51f1a78753faf7
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Reaction notes

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