Benzaldehyde → HCID 54516199, compound

HRID 580614Notes

Reaction equation

HRID 580614 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:12]([CH3:19])=[CH:13][C:14](OCC)=O.C(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.C(=O)([O-])[O-:35].[Na+].[Na+]>CN(C)C=O.O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:12]([CH:13]=[CH:14][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:19][CH2:5][C:2]([OH:35])=[O:4])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

8

Reactant 5

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 23665647Potassium tert-butoxideHCID 54026566HCID 54026566, compound

Product 1

HCID 54516199HCID 54516199, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

5.05 g (45 mmols) of potassium tert. butoxide were dissolved in 20 ml of absolute dimethylformamide, and a solution of 10.0 g (40 mmols) of ethyl 3,4-dimethoxy-β-methylcinnamate and 4.78 g (45 mmols) of benzaldehyde in 10 ml of absolute dimethylformamide was added dropwise thereto, while stirring and cooling on an ice bath. The mixture was then stirred for 4 hours at room temperature, combined with water and acidified with hydrochloric acid. The greasy substance obtained thereby was stirred with hot water, and sodium carbonate was added in batches until a solution was obtained. This aqueous solution was extracted twice with toluene. Upon acidification with hydrochloric acid, the product was precipitated, and after washing with water it was recrystallized from toluene.

Workup

  1. temperaturecooling on an ice bath
  2. stirringThe mixture was then stirred for 4 hours at room temperature
  3. customThe greasy substance obtained
  4. additionwas added in batches until a solution
  5. customwas obtained
  6. extractionThis aqueous solution was extracted twice with toluene
  7. customUpon acidification with hydrochloric acid, the product was precipitated
  8. washafter washing with water it
  9. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-f41bd5a2ed90422fae6d6889d77ecf03
Source dataset
uspto-grants-1988_06
Patent number
US04753934

Reaction notes

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