Water → HCID 58463234, compound

HRID 2383334Notes

Reaction equation

HRID 2383334 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O:18]C)(=[O:17])[CH2:11][CH2:12][C:13]([O:15]C)=O.CC(C)([O-])C.[K+].O>O1CCCC1.C(OCC)C>[OH:15][C:13]1[C:9]2[C:2](=[CH:3][CH:4]=[C:5]([CH3:6])[CH:8]=2)[CH:1]=[C:11]([C:10]([OH:18])=[O:17])[CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 77254-MethylbenzaldehydeHCID 7820Dimethyl SuccinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 58463234HCID 58463234, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methylbenzaldehyde (0.70 g) and dimethyl succinate (0.95 g) in tetrahydrofuran (15 mL) was added potassium tert-butoxide (0.73 g) at room temperature, and the reaction mixture was stirred overnight. To the reaction mixture were added water and diethyl ether, and the two layers were separated. The aqueous layer was acidified with 1 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. This organic layer was washed with a saturated sodium carbonate aqueous solution. The aqueous layer was acidified with 1 mol/L hydrochloric acid, and the mixture was extracted with diethyl ether. The organic layer was dried over magnesium sulfate, and concentrated. To the residue were added acetic acid (5 mL), acetic anhydride (5 mL) and sodium acetate (3.0 g), and the mixture was heated under reflux for 6 hours. After cooling to room temperature, the reaction mixture was poured into water. The resulting mixture was extracted with diethyl ether. The organic layer was washed with water and a saturated sodium hydrogen carbonate aqueous solution, and concentrated. To the obtained residue were added methanol (20 mL) and 1 mol/L sodium hydroxide aqueous solution (20 mL), and the mixture was heated under reflux for 5 hours. After the reaction mixture was cooled to room temperature, methanol was removed under reduced pressure. The obtained solution was acidified with 2 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to give the title compound (0.20 g).

Workup

  1. customthe two layers were separated
  2. extractionthe resulting mixture was extracted with diethyl ether
  3. washThis organic layer was washed with a saturated sodium carbonate aqueous solution
  4. extractionthe mixture was extracted with diethyl ether
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. additionTo the residue were added acetic acid (5 mL), acetic anhydride (5 mL) and sodium acetate (3.0 g)
  8. temperaturethe mixture was heated
  9. temperatureunder reflux for 6 hours
  10. additionthe reaction mixture was poured into water
  11. extractionThe resulting mixture was extracted with diethyl ether
  12. washThe organic layer was washed with water
  13. concentrationa saturated sodium hydrogen carbonate aqueous solution, and concentrated
  14. additionTo the obtained residue were added methanol (20 mL) and 1 mol/L sodium hydroxide aqueous solution (20 mL)
  15. temperaturethe mixture was heated
  16. temperatureunder reflux for 5 hours
  17. temperatureAfter the reaction mixture was cooled to room temperature
  18. custommethanol was removed under reduced pressure
  19. extractionthe resulting mixture was extracted with ethyl acetate
  20. washThe organic layer was washed with water
  21. dry with materialdried over magnesium sulfate
  22. concentrationconcentrated

Sources & evidence

ORD record
ord-5e03fbca44f64c51b264a1ced2d0ea70
Source dataset
uspto-grants-2012_09
Patent number
US08263622B2

Reaction notes

Loading…