Acetone → HCID 53727405, compound

HRID 1937775Notes

Reaction equation

HRID 1937775 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].OS(O)(=O)=O.[C:20]([O-])([O-])=O.[K+].[K+].[CH3:26][C:27]([CH3:29])=[O:28]>CO>[O:28]1[CH2:26][C@@H:27]1[CH2:29][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:20])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 4473644-Hydroxy-3-nitrophenylacetic acid

Product 1

HCID 53727405HCID 53727405, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The material purchased from Aldrich, 4-hydroxy-3-nitrophenyl acetic acid, (0.500 g, 2.54 mmol) was dissolved in methanol (5 mL) and was treated with concentrated H2SO4 (0.25 mL) at reflux for 16 h. The mixture was cooled, evaporated, taken up in 5% NaHCO3 and extracted into ethyl ether. A mixture of this crude compound (0.512 g, 2.43 mmol), K2CO3 (1.0 g, 7.27 mmol) and 2R-(−)-glycidyl-3-nitrobenzenesulfonate (0.630 g, 2.43 mmol) in acetone (10 mL) was refluxed for 24 h. The mixture was cooled, concentrated and purified by flash column chromatography (50% EtOAc/Hexane) to afford the title compound (0.59 g) as an off-white foam. 1H-NMR (250 MHz, CDCl3): δ 2.84-2.93 (m, 2H), 3.37-3.450(m, 1H), 3.62 (s, 2H), 3.71 (s, 3H), 4.09-4.16 (m, 1H), 4.37-4.42 (m, 1H), 7.1-7.8 (m, 3H).

Workup

  1. temperatureat reflux for 16 h
  2. temperatureThe mixture was cooled
  3. customevaporated
  4. extractionextracted into ethyl ether
  5. temperaturewas refluxed for 24 h
  6. temperatureThe mixture was cooled
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (50% EtOAc/Hexane)

Sources & evidence

ORD record
ord-bde099e3b7c5481db7c76512cefaab93
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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