Nitric Acid → HCID 57742139, compound

HRID 660323Notes

Reaction equation

HRID 660323 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[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:12]=[CH:11][C:10]([N+:15]([O-:17])=[O:16])=[C:9]([OH:13])[CH:8]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 13356241HCID 13356241, compound

Product 1

HCID 57742139HCID 57742139, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-(3-Hydroxy-phenyl)-propionic acid ethyl ester (19.0 g) in acetic acid (150 mL) was added nitric acid (11.3 g) at room temperature. The reaction mixture was stirred for 1 h 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 solid. (6.08 g, 26.0%)

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-006af1c787c4479ea159671ebdf48058
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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