2,5-Dimethoxybenzaldehyde → 2,5-DIMETHOXYBENZALDEHYDE OXIME

HRID 1170773Notes

Reaction equation

HRID 1170773 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH:5]=O.[NH2:13][OH:14].Cl.C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH:5]=[N:13][OH:14]

Participants

6

Reactant 3

HCID 667262,5-DimethoxybenzaldehydeHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 27557912,5-DIMETHOXYBENZALDEHYDE OXIMEYield 82.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

To 16.6 g (99.9 mmol) of 2,5-dimethoxybenzaldehyde in ethanol (100 mL) is added a mixture of 7.64 g (169 mmol) of H2NOH—HCl and 13.9 g (169 mmol) of sodium acetate in 50 mL of H2O. This reaction mixture is heated to reflux for 2.5 h. After adding H2O to dissolve the precipitated inorganic salt, ethanol is removed by evaporation in vacuo. The resulting white solid is filtered off and washed with H2O. 14.9 g of white solid are obtained (82%). 1H-NMR (CDCl3). δ [ppm]: 3.79 (s, 3H), 3.82 (s, 3H), 6.85 (d, 1H), 6.92 (d, 1H), 7.25 (d, 1H), 8.00 (broad s, 1H), 8.47 (s, 1H).

Workup

  1. temperatureThis reaction mixture is heated
  2. temperatureto reflux for 2.5 h
  3. customis removed by evaporation in vacuo
  4. filtrationThe resulting white solid is filtered off
  5. washwashed with H2O

Sources & evidence

ORD record
ord-7300f540919a45889b55b6071610ae37
Source dataset
uspto-grants-2010_11
Patent number
US07829257B2

Reaction notes

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