Potassium Hydroxide → HCID 20304493, compound

HRID 918092Notes

Reaction equation

HRID 918092 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[O:20][CH:11]2[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].[OH-].[K+]>C(O)C>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11](=[O:20])[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:8][CH:9]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20304490HCID 20304490, compound

Product 1

HCID 20304493HCID 20304493, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 5.63 g of 3-(4-carboxyphenyl)-1-phenyl-2,3-epoxy-1-propanone in 100 ml of ethanol at 85°-90°C was added a solution of 6 g of potassium hydroxide in 100 ml of ethanol with stirring over 5 min. The reaction mixture was heated at 85°-90°C for 5 min. and then allowed to cool to room temperature. The solution was evaporated to dryness and the residue was dissolved in 300 ml of ice-water and acidified with 125 ml of hydrochloric acid. After stirring for 30 min., the precipitate was collected and washed with water. The precipitate was dissolved in 600 ml of ethyl acetate and the solution was dried and filtered. The filtrate was evaporated to give 5.63 g (100%) of 3-(4-carboxyphenyl)-1-phenyl-1,2-propanedione as a yellow solid.

Workup

  1. temperatureThe reaction mixture was heated at 85°-90°C for 5 min.
  2. customThe solution was evaporated to dryness
  3. dissolutionthe residue was dissolved in 300 ml of ice-water
  4. stirringAfter stirring for 30 min.
  5. customthe precipitate was collected
  6. washwashed with water
  7. dissolutionThe precipitate was dissolved in 600 ml of ethyl acetate
  8. customthe solution was dried
  9. filtrationfiltered
  10. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-4a68c45475ab4f3d8d240a1d0f39e66e
Source dataset
uspto-grants-1976_07
Patent number
US03969373

Reaction notes

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