Benzaldehyde → Butanal, 2-(phenylmethylene)-

HRID 1024359Notes

Reaction equation

HRID 1024359 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH:11](=[O:15])[CH2:12][CH2:13][CH3:14].Cl>CCO>[CH:1](=[C:12]([CH2:13][CH3:14])[CH:11]=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 261ButanalHCID 313Hydrochloric AcidHCID 14797Potassium Hydroxide

Product 1

HCID 97782Butanal, 2-(phenylmethylene)-Yield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

30.0 mL Benzaldehyde was dissolved in 150 mL EtOH and cooled with an ice bath. Added was 5.01 mL. 45% KOH (0.2 equiv.), followed by dropwise addition of 16.5 mL butyraldehyde. The mixture was stirred for 3 days at room temperature, acidified with 1M HCl and extracted with ether. The organic layer was dried over Na2SO4, filtrated and concentrated in vacuo. Vacuum destillation yielded 20.4 g of a yellow fluid (78-82° C., 0.6 mbar) containing 70% of the desired product. This material was used in subsequent steps without further purification. Characteristic signals in 1H NMR (400 MHz, CDCl3): δ 1.15 (t, J=7.5 Hz, 3H), 2.57 (q, J=7.5 Hz, 1H), 7.22 (s, 1H), 9.56 (s, 1H).

Workup

  1. temperaturecooled with an ice bath
  2. additionAdded
  3. extractionextracted with ether
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customVacuum destillation yielded 20.4 g of a yellow fluid (78-82° C., 0.6 mbar)

Sources & evidence

ORD record
ord-0bfe445a8ec84dad96c263e71d087e48
Source dataset
uspto-grants-2014_05
Patent number
US08722887B2

Reaction notes

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