Acetonitrile → 2-methoxy-1,3-benzenedicarboxaldehyde

HRID 2389234Notes

Reaction equation

HRID 2389234 reaction equation
[OH:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]=[O:11].S(OC)(O[CH3:16])(=O)=O.C(#N)C.C(=O)([O-])[O-].[K+].[K+]>C(OCC)C>[CH3:16][O:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]=[O:11]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 3455542-Hydroxyisophthalaldehyde

Product 1

HCID 109538612-methoxy-1,3-benzenedicarboxaldehydeYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
75 °C

Procedure

2-Hydroxy-1,3-benzenedicarboxaldehyde (1.05 g, 7 mmol), dimethyl sulfate (1.06 g, 8.4 mmol), and 55 mL of acetonitrile were charged into a 1-necked flask equipped with a mechanical stirrer. 1.45 g (10.5 mmol) of potassium carbonate was added at room temperature under nitrogen. The mixture was stirred at 75° C. until GC-MS indicated that the reaction was complete. The reaction mixture was cooled to ambient temperature, diluted with diethyl ether, washed with NaCl/H2O, and dried over MgSO4. The ether was evaporated off. The crude product was recrystallized from diethyl ether. Pale yellow solid (0.62 g, 54% yield) was obtained. 1H NMR in CDCl3 was consistent with the proposed structure. 1H NMR (CDCl3): δ 10.4 (2H), 8.1 (2H), 7.4 (1H), 4.1 (3H).

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. washwashed with NaCl/H2O
  4. dry with materialdried over MgSO4
  5. customThe ether was evaporated off
  6. customThe crude product was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-84859954082242a49cf9a55f9f643f0a
Source dataset
uspto-grants-2012_09
Patent number
US08273678B2

Reaction notes

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