Vanillin → HCID 790176, compound

HRID 2308129Notes

Reaction equation

HRID 2308129 reaction equation
N1CCCCC1.O=[CH:8][C:9]1[CH:17]=[CH:16][C:14]([OH:15])=[C:11]([O:12][CH3:13])[CH:10]=1.[CH3:18][O:19][C:20](=[O:24])[CH2:21][C:22]#[N:23]>C(O)C>[CH3:18][O:19][C:20](=[O:24])/[C:21](/[C:22]#[N:23])=[CH:8]/[C:9]1[CH:17]=[CH:16][C:14]([OH:15])=[C:11]([O:12][CH3:13])[CH:10]=1

Participants

5

Reactant 3

HCID 1183VanillinHCID 7747Methyl cyanoacetateHCID 8082Piperidine

Product 1

HCID 790176HCID 790176, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.2 ml of piperidine were added carefully to a solution of 4.6 g (30 mmol) of vanillin, 3.4 ml (30.3 mmol) of cyanoacetic acid methyl ester and 0.5 ml of ethanol held at 45° C. The product started to precipitate on cooling to room temperature. The cold reaction mixture was diluted with 8 ml of ethanol, filtered and washed with cold ethanol to give 6.5 g (93%) of 2-cyano-(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid methyl ester in form of yellow crystals.

Workup

  1. customheld at 45° C
  2. customto precipitate
  3. customThe cold reaction mixture
  4. filtrationfiltered
  5. washwashed with cold ethanol

Sources & evidence

ORD record
ord-50662d62046e48758ec2f600c56e16bf
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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