Acetic Anhydride → HCID 735605, compound

HRID 1658516Notes

Reaction equation

HRID 1658516 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.C(OC(=O)C)(=O)C>>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[CH:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 79634-MethylpyridineHCID 312444-Methoxybenzaldehyde

Product 1

HCID 735605HCID 735605, compound

Procedure

A mixture of 4-picoline (280 g, 3.0 moles), p-methoxybenzaldehyde (410 g, 3.0 moles), and 500 ml. of acetic anhydride is refluxed for 24 hours, cooled, evaporated in vacuo, and the residue taken up in water and basified with 10% NaOH. The solid is filtered and crystallized from ethanol and water to give 350 g (55%) of the crude base. Recrystallization gives pure 4-(p-methoxystyryl)-pyridine, mp 128°-130°.

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. filtrationThe solid is filtered
  4. customcrystallized from ethanol and water
  5. customto give 350 g (55%) of the crude base
  6. customRecrystallization

Sources & evidence

ORD record
ord-5ddee59f779546caa3f7198b0143904c
Source dataset
uspto-grants-1976_06
Patent number
US03965102

Reaction notes

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