Acetic Acid → 4,4'-Dimethoxybenzil

HRID 1654248Notes

Reaction equation

HRID 1654248 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[O:12])=[O:10])=[CH:5][CH:4]=1.[N+]([O-])([O-])=O.[NH4+].C(O)(=O)C>O>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[OH:10])=[O:12])=[CH:18][CH:17]=1.[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[O:10])=[O:12])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 22985Ammonium nitrateHCID 710434,4'-Dimethoxybenzil

Product 2

HCID 710434,4'-DimethoxybenzilHCID 954154,4'-Dimethoxybenzoin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,4'-Dimethoxybenzoin was prepared as described in Example 1. 4,4'-Dimethoxybenzil (50.3 g), ammonium nitrate (20.3 g), cupric acetate (0.69 g) and 150 ml 80% acetic acid were heated to 80° C. with vigorous stirring until a clear, green solution was obtained. Following 1 hour at reflux, the mixture was poured into 1 liter of water and the precipitate was collected. Recrystallization from hot methanol afforded 4,4'-dimethoxybenzil. Yield 44.2 g (88%). 1H NMR (CDCl3) δ7.97 (m, 4H, aromatic), 6.97 (m, 4H, aromatic, 3.86 (s, 6H OMe).

Workup

  1. customwas obtained
  2. temperatureat reflux
  3. customthe precipitate was collected
  4. customRecrystallization from hot methanol

Sources & evidence

ORD record
ord-d23a966e2df34b0ba4c12b4fef436c59
Source dataset
uspto-grants-1995_04
Patent number
US05405926

Reaction notes

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