Hydrochloric Acid → 4-(2-(4-Formylphenyl)-ethenyl)-pyridine

HRID 1729123Notes

Reaction equation

HRID 1729123 reaction equation
[CH:1]1[C:6]([CH:7]=O)=[CH:5][CH:4]=[C:3]([CH:9]=[O:10])[CH:2]=1.C(OC(=O)C)(=O)C.[N:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.Cl>C(O)(=O)C>[CH:9]([C:3]1[CH:2]=[CH:1][C:6]([CH:7]=[CH:24][C:21]2[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=2)=[CH:5][CH:4]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 79634-MethylpyridineHCID 12173Terephthalaldehyde

Product 1

HCID 6021004-(2-(4-Formylphenyl)-ethenyl)-pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 400 parts of terephthaldehyde, 120 parts of acetic acid and 300 parts of acetic anhydride was refluxed for two hours. 188 parts of 4-picoline were then added over a period of 45 minutes, and the dark brown mixture was refluxed for a further 2 hours. 3300 parts of 1M aqueous hydrochloric acid were then added. The desired product was extracted with toluene and treated with 5M sodium hydroxide to a pH between 5 and 6. The crude solid product was dissolved in hot ethyl acetate and the solution was filtered. Cooling of the filtrate gave the desired product, 4-(2-(4-formylphenyl)-ethenyl)-pyridine.

Workup

  1. temperaturewas refluxed for two hours
  2. temperaturethe dark brown mixture was refluxed for a further 2 hours
  3. extractionThe desired product was extracted with toluene
  4. additiontreated with 5M sodium hydroxide to a pH between 5 and 6
  5. dissolutionThe crude solid product was dissolved in hot ethyl acetate
  6. filtrationthe solution was filtered
  7. temperatureCooling of the filtrate

Sources & evidence

ORD record
ord-fc71347aa22b47339e5d0fa9f381b02c
Source dataset
uspto-grants-1994_07
Patent number
US05332651

Reaction notes

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