Hydrochloric Acid → Ethyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoate

HRID 1610542Notes

Reaction equation

HRID 1610542 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)=[O:3].C(O)C.[H-].[Na+].Cl.[C:24](=O)([O:28]CC)[O:25][CH2:26][CH3:27]>O>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][C:24]([O:25][CH2:26][CH3:27])=[O:28])=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Product 1

HCID 4316945Ethyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-benzyloxyacetophenone (36 g, 159 mmol) in diethyl carbonate (200 ml) was added ethanol (0.6 ml) and sodium hydride (60% in oil, 12.7 g, 318 mmol) was added under ice-cooling. The mixture was stirred at room temperature for 2 hrs. To the reaction solution was added 6N hydrochloric acid to stop the reaction, and water (500 ml) was added. Then, the mixture was extracted with ethyl acetate (500 ml×2). The extract was washed successively with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) and recrystallized from ethyl acetate-hexane to give the objective substance (49.3 g, 100%).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. additionwas added
  4. extractionThen, the mixture was extracted with ethyl acetate (500 ml×2)
  5. washThe extract was washed successively with water and saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  9. customrecrystallized from ethyl acetate-hexane
  10. customto give the objective substance (49.3 g, 100%)

Sources & evidence

ORD record
ord-f6427184f9f947e592d436bac8e3bcc2
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…