Carbon Dioxide → Phenylbenzylglyoxal

HRID 259432

Reaction equation

HRID 259432 reaction equation
[C:1]1([C:7](=[O:17])[CH:8]2[O:10][CH:9]2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].O.C(=O)=O>C(O)C>[C:1]1([C:7](=[O:17])[C:8](=[O:10])[CH2:9][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 280Carbon Dioxide2×HCID 962WaterHCID 92219Chalcone epoxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 11096234PhenylbenzylglyoxalYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a boiling solution of 30 g 1,3-diphenyl-2,3-epoxy-1-propanone in 500 ml ethanol was rapidly added a hot solution of 30 g potassium t-butoxide in 500 ml ethanol. The mixture was kept boiling on a steambath for 2 minutes. It was then diluted with 3 l. water. The aqueous solution was saturated with carbon dioxide by the addition of small pieces of dry ice. The resulting emulsion was extracted with ether. The ether extracts were diluted with benzene, dried over sodium sulfate and evaporated under reduced pressure. The remaining dark oil was distilled in high vacuum to afford 19.5 g 1,3-diphenyl-1,2-propanedione; b.p. 136°-138° /0.1 mm.

Workup

  1. additionIt was then diluted with 3 l
  2. extractionThe resulting emulsion was extracted with ether
  3. additionThe ether extracts were diluted with benzene
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. distillationThe remaining dark oil was distilled in high vacuum

Sources & evidence

ORD record
ord-25a0ec43aa41454b824883ddc6523e3f
Source dataset
uspto-grants-1977_07
Patent number
US04038289

Linked notes

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