2,3-Dimethoxybenzaldehyde → HCID 73886677, compound

HRID 2185691Notes

Reaction equation

HRID 2185691 reaction equation
[Na].[CH3:2][O:3][C:4]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O.[N:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16]>C(O)C>[N:14]([C:17](=[CH:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:4]=1[O:3][CH3:2])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N+:15]=[N-:16]

Participants

5

Reactant 3

HCID 665812,3-DimethoxybenzaldehydeHCID 69480Acetic acid, azido-, ethyl esterHCID 5360545Sodium

Product 1

HCID 73886677HCID 73886677, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-18 °C

Procedure

Pieces of sodium (3.678 g, 160 mmol) were added to ethanol (200 ml) over a period of 30 minutes. The resulting solution was cooled to −18° C. and a mixture of 2,3-dimethoxybenzaldehyde (4.832 g, 40 mmol) and ethyl azidoacetate (20.64 g, 160 mmol) was then added, over one hour, at a rate which allowed the temperature to be maintained below −15° C. After three hours, the solution was stored at 5° C. for two days in order to give a crystalline product which was collected. and washed with cold hexane in order to give a pure product in the form of a yellow oil.

Workup

  1. additionwas then added, over one hour, at a rate which
  2. temperatureto be maintained below −15° C
  3. waitthe solution was stored at 5° C. for two days in order
  4. customto give a crystalline product which
  5. customwas collected
  6. washand washed with cold hexane in order
  7. customto give a pure product in the form of a yellow oil

Sources & evidence

ORD record
ord-6d8c19f2725b449d890dbcc10154b74a
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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