Nitric Acid → Ethyl 2-(4-hydroxy-3-nitrophenyl)propanoate

HRID 1626851Notes

Reaction equation

HRID 1626851 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 12785115Ethyl 2-(4-hydroxyphenyl)propanoate

Product 1

HCID 21444155Ethyl 2-(4-hydroxy-3-nitrophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 2-(4-hydroxyphenyl)propanoate (275 mg, 1.42 mmol) in acetic acid (2 mL) was added nitric acid (60-62%, 300 mg, 2.86 mmol) at room temperature. The mixture was stirred for 1 hour at 50° C. and cooled to room temperature. The reaction mixture was poured into ice water (20 mL) and extracted with EtOAc. The organic layer was dried with MgSO4 and filtered. EtOAc was removed by evaporation. The residue was purified by column chromatography eluting with n-Hexane/EtOAc=6/1.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customEtOAc was removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with n-Hexane/EtOAc=6/1

Sources & evidence

ORD record
ord-e3c1dd926de7413db7d20849d2e10861
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

Loading…