Vanillin → HCID 136138631, compound

HRID 326171Notes

Reaction equation

HRID 326171 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.O=[CH:13][C:14]1[CH:22]=[CH:21][C:19]([OH:20])=[C:16]([O:17][CH3:18])[CH:15]=1>C(OC(=O)C)(=O)C>[OH:20][C:19]1[CH:21]=[CH:22][C:14]([CH:13]=[CH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:15][C:16]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 1183VanillinHCID 102854-Methylquinoline

Product 1

HCID 136138631HCID 136138631, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

In 62.9 g of acetic anhydride, 26.73 g of 4-methylquinoline and 31.25 g of vanillin were refluxed overnight. The resultant reaction mixture was treated with an alkali. The product thus obtained was recrystallized via butyl cellosolve, to afford 29 g of 4-[2-(4-hydroxy-3-methoxyphenyl)-ethenyl]-quinoline having a melting point of 217°-219° C. From 0.55 g of this product, 1.75 g of triethylamine, 1.66 g of methacrylic acid chloride, and 16 cm3 of N,N-dimethylacetamide, there was obtained 4.70 g (80.3% in yield) of 4[2-(4-methacroyloxy-3-methoxyphenyl)-ethenyl]-quinoline having a melting point of 134°-135° C. This product was recrystallized via ethyl acetate and assayed by infrared absorption spectrometry and elementary analysis for its chemical structure.

Workup

  1. customThe resultant reaction mixture
  2. additionwas treated with an alkali
  3. customThe product thus obtained
  4. customwas recrystallized via butyl cellosolve

Sources & evidence

ORD record
ord-631c482ce57d4b37b82f7681c93834c8
Source dataset
uspto-grants-1984_04
Patent number
US04444868

Reaction notes

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