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

HRID 660315Notes

Reaction equation

HRID 660315 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[N+:15]([O-])([OH:17])=[O:16].O>C(O)(=O)C>[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 12785115Ethyl 2-(4-hydroxyphenyl)propanoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(4-hydroxy-phenyl)-propionic acid ethyl ester (9.02 g) in acetic acid (75 mL) was added nitric acid (60%, 5.24 g in AcOH) at room temperature. The reaction mixture was stirred for 30 minutes at room temperature and added water. The mixture was extracted with EtOAc and the organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1) to afford the product as yellow oil. (9.71 g)

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1)

Sources & evidence

ORD record
ord-a507f1f146284096a9b5e5b2c74d9f84
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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