Hydrochloric Acid → 1,2,3-triphenylpropane-1,3-dione

HRID 1160052Notes

Reaction equation

HRID 1160052 reaction equation
[H-].[Na+].[C:3]1([C:9]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:18](OC)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>O.C1(C)C=CC=CC=1>[C:19]1([C:18](=[O:25])[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:10])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7150Methyl BenzoateHCID 99482-PhenylacetophenoneHCID 24758Sodium hydride

Product 1

HCID 34690551,2,3-triphenylpropane-1,3-dioneYield 60.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

In a 500-ml four-necked flask were placed 16.0 g (0.40 mole) of 60% sodium hydride (an oil-added grade), 39.6 g (0.20 mole) of deoxybenzoin, 200.0 g of toluene, and 198.8 g (1.46 moles) of methyl benzoate. The mixture was then heated under reflux with stirring for 15 hours while distilling off methanol. After the reaction was over, the reaction mixture was cooled to 40° C. and 60.8 g (0.60 mole) of concentrated hydrochloric acid and 180.0 g of water were added in drops. The reaction mixture was transferred to a separatory funnel and an organic layer was separated. The organic layer was concentrated under reduced pressure to dryness. The residue was purified by reslurrying with methanol and a solid was recovered by filtration and dried under reduced pressure to give 36.2 g of 1,2,3-triphenylpropane-1,3-dione.

Workup

  1. customIn a 500-ml four-necked flask were placed
  2. temperatureThe mixture was then heated
  3. temperatureunder reflux
  4. distillationwhile distilling off methanol
  5. customThe reaction mixture was transferred to a separatory funnel
  6. customan organic layer was separated
  7. concentrationThe organic layer was concentrated under reduced pressure to dryness
  8. customThe residue was purified
  9. filtrationa solid was recovered by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-2ed9e9d5bbf348f49d84226fe523895c
Source dataset
uspto-grants-2010_10
Patent number
US07816020B2

Reaction notes

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