Sodium Carbonate → 4-Methoxy-3,5-dimethylbenzaldehyde oxime

HRID 2425299Notes

Reaction equation

HRID 2425299 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[CH3:12].Cl.[NH2:14][OH:15].C([O-])([O-])=O.[Na+].[Na+]>C(O)C.CCOC(C)=O>[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:6]([CH:7]=[N:14][OH:15])=[CH:5][C:4]=1[CH3:12]

Participants

6

Reactant 3

HCID 10340Sodium Carbonate2×HCID 443297Hydroxyamine hydrochloride2×HCID 27585734-Methoxy-3,5-dimethylbenzaldehyde

Product 1

HCID 724690044-Methoxy-3,5-dimethylbenzaldehyde oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

4-Methoxy-3,5-dimethylbenzaldehyde (1.86 g, 11.3 mmol) was dissolved in ethanol (30 mL) and stirred with hydroxylamine hydrochloride (2.4 M aq. solution, 5.65 mL, 1.2 eq.) and Na2CO3 (1.2 M solution, 5.65 mL, 0.6 eq.) at room temperature for 2.5 hours. The mixture was then heated to 60° C. and additional hydroxylamine hydrochloride and Na2CO3 was added. The mixture was again stirred overnight at 60° C., transferred to a separatory funnel, diluted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4, filtered and concentrated. The product was purified by ISCO chromatography with EtOAc/hexanes eluent to yield 1.55 g (8.56 mmol) of 4-methoxy-3,5-dimethylbenzaldehyde oxime as a white solid. M+1=180.0.

Workup

  1. customtransferred to a separatory funnel
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by ISCO chromatography with EtOAc/hexanes eluent

Sources & evidence

ORD record
ord-325efda0717b49c688173281016c3730
Source dataset
uspto-grants-2011_06
Patent number
US07964624B1

Reaction notes

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