Benzaldehyde → Butanal, 2-(phenylmethylene)-

HRID 12498Notes

Reaction equation

HRID 12498 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 distillation 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. distillationVacuum distillation
  8. customyielded 20.4 g of a yellow fluid (78-82° C., 0.6 mbar)

Sources & evidence

ORD record
ord-d24af1c2c83e4a5d85276af70c02367d
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Reaction notes

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