Acrolein → HCID 86657638, compound

HRID 217426Notes

Reaction equation

HRID 217426 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[CH:14][C:13]=2[O:21][CH3:22])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C([O-])([O-])=O.[K+].[K+].[CH:29]([CH:31]=[CH2:32])=[O:30]>O1CCOCC1>[CH3:22][O:21][C:13]1[CH:14]=[C:15]([CH2:18][CH2:19][CH3:20])[CH:16]=[CH:17][C:12]=1[O:11][CH2:10][C:8]1[CH:9]=[C:2]2[C:3]([CH:4]=[C:31]([CH:29]=[O:30])[CH2:32][O:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7847AcroleinHCID 11430Potassium CarbonateHCID 58439092HCID 58439092, compound

Product 1

HCID 86657638HCID 86657638, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-hydroxy-4-[(2-methoxy-4-propylphenoxy)methyl]benzaldehyde (120 mg) in dioxane (2.4 mL) were added K2CO3 (55.2 mg) and acrolein (0.267 mL) at 25° C. The reaction mixture was warmed to 100° C., followed by stirring at 100° C. for 15 hours. The reaction mixture was left to be cooled to 25° C., and then filtered through celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 80:20) to obtain 7-[(2-methoxy-4-propylphenoxy)methyl]-2H-chromene-3-carbaldehyde (104.2 mg) as a colorless liquid.

Workup

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to 25° C.
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=100:0 to 80:20)

Sources & evidence

ORD record
ord-567d53b2e03a457d995931f1e3cb573d
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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