Water → HCID 3313391, compound

HRID 1940685Notes

Reaction equation

HRID 1940685 reaction equation
[O:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[OH:12])[CH:7]=O)[CH2:2][CH3:3].[C:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])#[N:14].N1CCCCC1.O>C(O)C>[C:13]([C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]1[CH:9]=[CH:10][C:11]([OH:12])=[C:4]([O:1][CH2:2][CH3:3])[CH:5]=1)#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 7747Methyl cyanoacetateHCID 8082PiperidineHCID 8467Ethylvanillin

Product 1

HCID 3313391HCID 3313391, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 20 grams of 3-ethoxyl-4-hydroxybenzaldhyde and 13 grams of methyl cyanoacetate in 100 ml of ethanol was refluxed with 1 ml of piperidine for 4 hours. The crude mixture was allowed to cool down to room temperature and, with stirring, water was added until the solid began to form. This mixture was then refrigerated for 4 hours and solids was collected by suction filtration, washed with a cold mixture of ethanol and water (1:2) and suction dried to provide 25 grams of 1-cyano-2-(3-ethoxy-4-hydroxyphenyl)-1-methoxycarbonyl ethene.

Workup

  1. customto form
  2. filtrationsolids was collected by suction filtration
  3. washwashed with a cold mixture of ethanol and water (1:2) and suction
  4. customdried

Sources & evidence

ORD record
ord-cb4935e2886547df8c394fcd502da210
Source dataset
uspto-grants-1997_12
Patent number
US05700822

Reaction notes

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