Nitric Acid → HCID 57742139, compound

HRID 660284Notes

Reaction equation

HRID 660284 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1.[N+:15]([O-])([OH:17])=[O:16].O>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 13356241HCID 13356241, compound

Product 1

HCID 57742139HCID 57742139, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of Ethyl 2-(3-hydroxyphenyl)propanoate (2.51 g, 12.9 mmol) in acetic acid (20 mL) was added nitric acid (1.45 g, 13.8 mmol) in acetic acid (2 mL) at room temperature. Then the colorless oil changed to the dark brown oil after 1˜2 minutes stirred. The reaction mixture was stirred for 15 minutes at room temperature then poured into iced water (100 mL), and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:6) as eluant. Yellow solid (m.p. 45-47° C.), yield: 30.8%

Workup

  1. waitThen the colorless oil changed to the dark brown oil after 1˜2 minutes
  2. stirringThe reaction mixture was stirred for 15 minutes at room temperature
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-9b93fe913a9d40f08db30487e4ab5f3a
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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