Acetaldehyde → HCID 4695677, compound

HRID 1616919Notes

Reaction equation

HRID 1616919 reaction equation
C(=O)C.[OH:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13](=[O:15])[CH3:14].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>>[CH2:21]([O:20][C:18](=[O:19])[CH2:17][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[C:13](=[O:15])[CH3:14])[CH3:22]

Participants

6

Reactant 5

HCID 177AcetaldehydeHCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11092PaeonolHCID 11430Potassium Carbonate

Product 1

HCID 4695677HCID 4695677, compound

Conditions

Temperature
90 °C

Procedure

Into a Round bottom flask was added Ethanone, 1-(2-hydroxy-4-methoxyphenyl)-ethanone (40.01 g, 0.241 mol), ethyl bromoacetate (28.17 mL, 0.2540 mol), potassium carbonate (69.6 g, 0.504 mol), and N,N-Dimethylformamide (200 mL, 2 mol). The reaction was heated at 90° C. for 6 h before cooling to RT overnight. The reaction was poured into ice/water and extracted with ethyl ether (twice). The combined ether extracts were dried, filtered and concentrated. The resulting solid was triturated in hexanes, filtered and dried. The product was used in the next reaction step without further purification.

Workup

  1. temperaturebefore cooling to RT overnight
  2. extractionextracted with ethyl ether (twice)
  3. dry with materialThe combined ether extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting solid was triturated in hexanes
  7. filtrationfiltered
  8. customdried
  9. customThe product was used in the next reaction step without further purification

Sources & evidence

ORD record
ord-5c43a5b735b0464696872dc87fa894d9
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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