Sodium Benzoate → 3-(Benzoyloxy)-2,4-pentanedione

HRID 1985742Notes

Reaction equation

HRID 1985742 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].Cl[CH2:12][C:13]([CH2:15][C:16](=[O:18])[CH3:17])=[O:14].CCCCCC.C(OCC)(=O)C>CS(C)=O.O>[C:13]([CH:15]([O:8][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:16](=[O:18])[CH3:17])(=[O:14])[CH3:12]

Participants

6

Reactant 3

HCID 517055Sodium BenzoateHCID 144968561-Chloro-2,4-pentanedioneHCID 21226206Ethyl acetate hexane

Product 1

HCID 207383-(Benzoyloxy)-2,4-pentanedione

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

Sodium benzoate (106.5 g, 0.74 mol) is suspended in 500 ml of dry DMSO in a three necked flask equipped with a mechanical stirrer and under a gentle stream of argon. Chloroacetylacetone (50 g, 0.37 mol) is then added and the resulting orange mixture is stirred vigorously. After 3 hours the reaction is complete (TLC hexane/ethyl acetate 8/2); the melange is cooled by means of iced water and diluted with 500 ml of water. The solution is then extracted into ether (3×400 ml), washed with water (2×1 L), dried over Na2SO4 and concentrated to dryness in vacuo. The resulting viscous orange oil is pure enough for the next step. The yield is 81.4 g (100%).

Workup

  1. customequipped with a mechanical stirrer and under a gentle stream of argon
  2. extractionThe solution is then extracted into ether (3×400 ml)
  3. washwashed with water (2×1 L)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-a6d5a2e35586424a8414602249abb628
Source dataset
uspto-grants-2009_06
Patent number
US07547709B2

Reaction notes

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