Acrolein → HCID 15391778, compound

HRID 428166Notes

Reaction equation

HRID 428166 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[CH:12]=O.[CH:14]([CH:16]=[CH2:17])=[O:15].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.ClCCl>[O:9]1[C:4]2=[C:3]3[C:2](=[CH:11][CH:10]=[C:5]2[O:6][CH2:7][CH2:8]1)[O:1][CH2:17][C:16]([CH:14]=[O:15])=[CH:12]3

Participants

6

Reactant 3

HCID 7847AcroleinHCID 11430Potassium CarbonateHCID 11805342HCID 11805342, compound

Product 1

HCID 15391778HCID 15391778, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

3 g (16.6 mmol) of the compound obtained in Step B and 1.4 g (25 mmol) of acrolein are added to a suspension of 3.48 g (25 mmol) of potassium carbonate in 40 ml of 1,4-dioxane; the medium is then heated at reflux under argon for 3 hours. After cooling and filtering off the salts, the solvent is evaporated in vacuo. The residue obtained is taken up in dichloromethane and then washed with water. The organic phase is dried over magnesium sulphate and then concentrated in vacuo. Chromatography on a silica column (eluant:ethyl acetate/petroleum ether 10/90) allows the title compound to be obtained in the form of a yellow solid.

Workup

  1. temperaturethe medium is then heated
  2. temperatureat reflux under argon for 3 hours
  3. temperatureAfter cooling
  4. filtrationfiltering off the salts
  5. customthe solvent is evaporated in vacuo
  6. customThe residue obtained
  7. washwashed with water
  8. dry with materialThe organic phase is dried over magnesium sulphate
  9. concentrationconcentrated in vacuo
  10. customto be obtained in the form of a yellow solid

Sources & evidence

ORD record
ord-1faa8f315a0f48c3be9996d89fa725f7
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Reaction notes

Loading…