Hydrochloric Acid → Dibenzoylmethane

HRID 544181Notes

Reaction equation

HRID 544181 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:10](OCC)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[NH2-].[Na+].[Na]>O1CCCC1>[C:11]1([C:10](=[O:17])[CH2:2][C:1]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:3])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7165Ethyl benzoateHCID 7410AcetophenoneHCID 24533Sodium amideHCID 5360545Sodium

Product 1

HCID 8433Dibenzoylmethane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution of acetophenone (6.2 g) is added to a tetrahydrofuran suspension of NaNH2 (4.0 g). The mixture is stirred at room temperature for ten minutes. Ethyl benzoate (15.5 g) is then added to the mixture. A gelatinous precipitate forms over the course of 24 hours. The mixture is added to an aqueous solution of HCl to neutralize the sodium amide and the sodium salt of the β-diketone. The mixture is then extracted with chloroform. The organic layer is stripped on a rotary evaporator. 1,3-diphenyl-1,3-propanedione is isolated from the residue by precipitating its copper salt. Decomposition of the complex with HCl yields the desired product in pure form. NMR analysis confirms the expected structure.

Workup

  1. customover the course of 24 hours
  2. extractionThe mixture is then extracted with chloroform
  3. customThe organic layer is stripped on a rotary evaporator

Sources & evidence

ORD record
ord-b5bb6ae28b924bf8b1e306ef3fe342b0
Source dataset
uspto-grants-1984_05
Patent number
US04448847

Reaction notes

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