4-Hydroxybenzaldehyde → HCID 682482, compound

HRID 326175Notes

Reaction equation

HRID 326175 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.Cl.N>C(OC(=O)C)(=O)C>[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[CH:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 222AmmoniaHCID 313Hydrochloric AcidHCID 79634-Methylpyridine

Product 1

HCID 682482HCID 682482, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

In 65.8 g of acetic anhydride, 20.0 g of γ-picolin and 26.2 g of p-hydroxybenzaldehyde were refluxed for 24 hours. The resultant reaction mixture and 100 ml of 6 N hydrochloric acid added thereto were further refluxed for 60 minutes and then cooled. The reaction product was neutralized by addition of aqueous ammonia and stirred for 1 hour. The yellow crystals which consequently deposited therein were separated by filtration. The crystals were recrystallized from a mixed solvent of ethanol and ether, to afford 35 g of 4-[2-(4-hydroxyphenyl)-ethenyl]-pyridine having a melting point of 272° to 275° C.

Workup

  1. additionadded
  2. temperaturethereto were further refluxed for 60 minutes
  3. temperaturecooled
  4. customThe yellow crystals which consequently deposited therein were separated by filtration
  5. customThe crystals were recrystallized from a mixed solvent of ethanol and ether

Sources & evidence

ORD record
ord-0058906b35ad4192b1bd407670a0ca5e
Source dataset
uspto-grants-1984_04
Patent number
US04444868

Reaction notes

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