Vanillin → HCID 616228, compound

HRID 1586628Notes

Reaction equation

HRID 1586628 reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[C:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])#[N:13]>N1CCCCC1.C(O)(=O)C.C(O)C>[C:12]([C:14](=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1)[C:15]([O:17][CH3:18])=[O:16])#[N:13]

Participants

6

Reactant 2

HCID 1183VanillinHCID 7747Methyl cyanoacetate

Product 1

HCID 616228HCID 616228, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A mixture of vanillin (7.60 g, 0.05 mol), methyl cyanoacetate (4.95 g, 0.05 mol), ethanol (50 mL), piperidine (12 drops) and acetic acid (6 drops) is heated at reflux for 3 hours with stirring and then cooled. The pale yellow product crystallizes and additional ethanol (25 mL) is added to promote stirring and 5% HCl (10 mL) is added to neutralize any phenol salt present. The product, methyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate, is collected by filtration, washed with ethanol and dried in air. A yield of 9.4 g (80.6%) is obtained. The identity of the product is supported by mass spectroscopy analysis and is shown below as compound I. ##STR16##

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. customThe pale yellow product crystallizes
  5. additionadditional ethanol (25 mL) is added
  6. stirringto promote stirring
  7. addition5% HCl (10 mL) is added
  8. filtrationThe product, methyl 2-cyano-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate, is collected by filtration
  9. washwashed with ethanol
  10. customdried in air
  11. customA yield of 9.4 g (80.6%) is obtained

Sources & evidence

ORD record
ord-8dff1346698747cbb1060f71f9c2f236
Source dataset
uspto-grants-1993_06
Patent number
US05215876

Reaction notes

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