Benzaldehyde → 5337-53-1

HRID 1815126Notes

Reaction equation

HRID 1815126 reaction equation
[OH-].[Na+].C(O)C.[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)(=[O:8])[CH3:7].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH:19]1[CH:20]=[CH:21][C:16](/[CH:15]=[CH:7]/[C:6]([C:9]2[N:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:8])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 702EthanolHCID 142862-AcetylpyridineHCID 14798Sodium Hydroxide

Product 1

HCID 53541195337-53-1

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of NaOH (12.8 mmol, 1.28 equiv.) in water (4.55 g) and ethanol (2.32 g) are introduced into a round bottom flask with a magnetic stirrer. Into the alkaline solution is placed 2-acetyl pyridine 1a (10 mmol, 1 equiv.) and the flask is rapidly surrounded by ice and the stirrer is started. The temperature reaches 10° C.-15° C. and benzaldehyde 1b (10 mmol, 1 equiv.) is added at once. The ice bath is removed and the reaction is stirred for 15 hours. The reaction is filtered. The filtrate is concentrated under reduced pressure and the product is purified by flash column chromatography on SiO2 (33% ethyl acetate/hexanes) to give the 3-phenyl-1-pyridin-2-yl-propenone 1c as a pale yellow solid. See Kohler, E. P. & H. M. Chadwell, H. M., Org. Synth., Coll. Vol. 1, 2nd ed., p. 78.

Workup

  1. customreaches 10° C.-15° C.
  2. customThe ice bath is removed
  3. filtrationThe reaction is filtered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe product is purified by flash column chromatography on SiO2 (33% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c403e5ab99ad4f84991ed747de072f39
Source dataset
uspto-grants-2005_04
Patent number
US06878729B2

Reaction notes

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