Benzaldehyde, 2-ethoxy- → HCID 85707528, compound

HRID 2185687Notes

Reaction equation

HRID 2185687 reaction equation
[Na].[CH2:2]([O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=O)[CH3:3].[N:13]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N+:14]=[N-:15]>C(O)C>[N:13]([C:16](=[CH:7][C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[O:4][CH2:2][CH3:3])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 11950Benzaldehyde, 2-ethoxy-HCID 69480Acetic acid, azido-, ethyl esterHCID 5360545Sodium

Product 1

HCID 85707528HCID 85707528, 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-ethoxybenzaldehyde (6.007 g, 40 mmol) and ethyl azidoacetate (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 an off-white solid.

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. washwashed with cold hexane in order
  7. customto give an off-white solid

Sources & evidence

ORD record
ord-a15eccad5bd842848b23ed451c56585f
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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