Ethyl cyanoacetate → HCID 53653792, compound

HRID 1586632Notes

Reaction equation

HRID 1586632 reaction equation
[C:1]([CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][C:9]=1[O:16][CH3:17])([O:3][CH2:4][CH3:5])=[O:2].[C:18]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:19].N1CCCCC1>C(O)C>[C:18]([C:20](=[CH:12][C:11]1[CH:14]=[CH:15][C:8]([O:7][CH2:6][C:1]([O:3][CH2:4][CH3:5])=[O:2])=[C:9]([O:16][CH3:17])[CH:10]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:19]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 968872Ethyl (4-formyl-2-methoxyphenoxy)acetate

Product 1

HCID 53653792HCID 53653792, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-carbethoxymethoxy-3-methoxybenzaldehyde (23.8 g, 0.10 mol), ethyl cyanoacetate (11.3 g, 0.10 mol), ethanol (150 mL) and piperidine (2 mL) is heated at reflux for 4 hours. The reaction mixture is allowed to cool, and the solid is collected by filtration, washed with ethanol and dried in air. A yield of 31.3 g (93%) of product is obtained which has the following structure as supported by mass spectrometry: ##STR21## An absorption maximum at 355 nm is observed when the product is dissolved in methylene chloride.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. temperatureto cool
  4. filtrationthe solid is collected by filtration
  5. washwashed with ethanol
  6. customdried in air

Sources & evidence

ORD record
ord-9b7f2899ada443eeb6acbbc363b24b82
Source dataset
uspto-grants-1993_06
Patent number
US05215876

Reaction notes

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