Sulfuric Acid → HCID 58374134, compound

HRID 2388166Notes

Reaction equation

HRID 2388166 reaction equation
O[N:2]=[C:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:4]([CH3:12])[C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>C(O)C>[CH3:12][C:4]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:2][O:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86648115Ethyl 4-(hydroxyimino)-3-methyl-2-oxo-4-phenylbutanoate

Product 1

HCID 58374134HCID 58374134, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(hydroxyimino)-3-methyl-2-oxo-4-phenylbutanoate (13.2 g, 53.0 mmol) and concentrated sulfuric acid (10 mL) were added to 150 mL of absolute ethanol and the mixture was refluxed for 20 hours. After the mixture cooled to room temperature, saturated sodium bicarbonate solution was added to neutralize the mixture. The product was extracted with EtOAc and the combined organic layers were dried over MgSO4 and concentrated to give 12.5 g of the title compound. MS: (+) m/z 232.46 (M+1).

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. extractionThe product was extracted with EtOAc
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9a4abe87720f47f2b2020927e0e94333
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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