Benzaldehyde → 2-Styrylpyridine

HRID 1720201Notes

Reaction equation

HRID 1720201 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][C:12](C)=[CH:11][CH:10]=1.[C:16](OC(=O)C)(=O)C>C(O)(=O)C.ClCCl>[CH:16]([C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 7918Acetic AnhydrideHCID 79634-Methylpyridine

Product 1

HCID 1363502-Styrylpyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A stirring solution of benzaldehyde (44.6 g) and 4-picoline (37.2 g) in acetic acid (24 g) and acetic anhydride (40.8 g) was refluxed for 18 hours. The resultant reaction mixture were cooled, diluted with dichloromethane (300 ml), washed with water and dilute aqueous alkali; and quenched with dilute hydrochloric acid. Precipitate of styrylpyridine hydrochloride (long golden needles) was separated by filtration, washed with methylenechloride, dried and poured into stirred solution of sodium carbonate in water. After 2 hours of stirring white-gray precipitate was filtered, washed with water and dried overnight at 60°-70° C. After recrystallization, 39.6 g. of styrylpyridine were obtained.

Workup

  1. customThe resultant reaction mixture
  2. temperaturewere cooled
  3. washwashed with water and dilute aqueous alkali
  4. customand quenched with dilute hydrochloric acid
  5. customPrecipitate of styrylpyridine hydrochloride (long golden needles) was separated by filtration
  6. washwashed with methylenechloride
  7. customdried
  8. additionpoured
  9. filtrationAfter 2 hours of stirring white-gray precipitate was filtered
  10. washwashed with water
  11. customdried overnight at 60°-70° C
  12. customAfter recrystallization, 39.6 g

Sources & evidence

ORD record
ord-03169e2c5c7c4796a41118d0de8929a6
Source dataset
uspto-grants-1996_04
Patent number
US05506089

Reaction notes

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