Hydrochloric Acid → 3-[4-(2-Carboxyethyl)phenyl]-1-phenyl-2,3-epoxy-1-propanone

HRID 259434Notes

Reaction equation

HRID 259434 reaction equation
[C:1]([CH2:4][CH2:5][C:6]1[CH:21]=[CH:20][C:9]([CH:10]=[CH:11][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:8][CH:7]=1)([OH:3])=[O:2].[OH:22]O.Cl>[OH-].[Na+]>[C:1]([CH2:4][CH2:5][C:6]1[CH:21]=[CH:20][C:9]([CH:10]2[O:22][CH:11]2[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:8][CH:7]=1)([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 543866524-(2-Carboxyethyl)benzalacetophenone

Product 1

HCID 203044873-[4-(2-Carboxyethyl)phenyl]-1-phenyl-2,3-epoxy-1-propanoneYield 55%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a suspension of 5.6 g of 4-(2-carboxyethyl)benzalacetophenone and 20 ml of 1N sodium hydroxide solution was added 4 ml of 30% hydrogen peroxide at room temperature. The mixture was cooled in an ice-bath and 15 ml of 0.5N sodium hydroxide solution was added dropwise over a few min. with stirring. The reaction mixture was stirred at room temperature for 3 hrs. and then the pH was adjusted from 9.4 to 4.5 by the addition of 1N hydrochloric acid. After about 1/2 hr., the precipitate was collected. The precipitate was dissolved in 200 ml of ethyl acetate, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated. The residue was dissolved in 100 ml of boiling ethyl acetate. About 50 ml of the solvent was evaporated and 50 ml of ether was added. The solution was concentrated to about 25 ml and after standing at room temperature for 17 hrs., the solid was collected, washed with 1:4-ethyl acetate-ether followed by ether and dried under vacuum at 60°-65° C. to give 3.3 g (55%) of 3-[4-(2-carboxyethyl)phenyl]-1-phenyl-2,3-epoxy-1-propanone as colorless crystals.

Workup

  1. temperatureThe mixture was cooled in an ice-bath
  2. stirringThe reaction mixture was stirred at room temperature for 3 hrs
  3. custom, the precipitate was collected
  4. dissolutionThe precipitate was dissolved in 200 ml of ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. dissolutionThe residue was dissolved in 100 ml of boiling ethyl acetate
  9. customAbout 50 ml of the solvent was evaporated
  10. addition50 ml of ether was added
  11. concentrationThe solution was concentrated to about 25 ml
  12. waitafter standing at room temperature for 17 hrs
  13. custom, the solid was collected
  14. washwashed with 1
  15. customdried under vacuum at 60°-65° C.

Sources & evidence

ORD record
ord-328e6892d6b847289a6faba0c6b595f4
Source dataset
uspto-grants-1977_07
Patent number
US04038289

Reaction notes

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