Levulinic Acid → HCID 18415149, compound

HRID 1978280Notes

Reaction equation

HRID 1978280 reaction equation
[C:1]1([NH:11]N=C(C2C=CC=CC=2)C2C=CC=CC=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:26](O)(=O)[CH2:27][CH2:28][C:29]([CH3:31])=[O:30].CC1C=CC(S(O)(=O)=O)=[CH:39][CH:40]=1.O.C([O-])(O)=[O:47].[Na+]>C(O)C.CCOCC>[CH2:39]([O:47][CH2:31][C:29]([C:28]1[C:2]2[C:1](=[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=2)[NH:11][C:27]=1[CH3:26])=[O:30])[CH3:40]

Participants

7

Reactant 4

HCID 11579Levulinic AcidHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 9883637HCID 9883637, compound

Product 1

HCID 18415149HCID 18415149, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

N-(1-Naphthyl)-benzophenone hydrazone (1.0 equiv., 1.0 mmol, 322 mg), levulinic acid (1.5 equiv., 1.5 mmol, 0.18 mL), and TsOH.H2O (2 equiv., 2 mmol mmol, 380 mg) were dissolved in ethanol (10 mL) and heated to reflux for 15 hours. The reaction mixture was then cooled to room temperature, diluted with Et2O (5 mL), neutralized with a saturated NaHCO3 solution, and extracted with Et2O (3×10 mL). The organic extracts were then dried over Na2SO4, filtered and concentrated under vacuum. Purification by flash column chromatography (20% EtOAc/Hex) gave the title product as a yellow oil (238 mg, 0.89 mmol, 89% yield).

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 hours
  3. extractionextracted with Et2O (3×10 mL)
  4. dry with materialThe organic extracts were then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customPurification by flash column chromatography (20% EtOAc/Hex)

Sources & evidence

ORD record
ord-f988e311ab974d5c9918ea868931da01
Source dataset
uspto-grants-2001_05
Patent number
US06235936B1

Reaction notes

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