Nitric Acid → Methyl 2-(4-hydroxy-3-nitrophenyl)acetate

HRID 660275Notes

Reaction equation

HRID 660275 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 518900Benzeneacetic acid, 4-hydroxy-, methyl ester

Product 1

HCID 1473109Methyl 2-(4-hydroxy-3-nitrophenyl)acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl-2-(4-hydroxyphenyl)acetate (2.0 g, 12.0 mmol) was dissolved in acetic acid (15 ml) and nitric acid (60-62%, 1.27 g, 12.1 mmol) was added at RT. The reaction mixture was stirred for 30 minutes at RT, poured into ice water (100 ml) and extracted with EA. The organic phase was dried over MgSO4, the solvent removed under a vacuum and the residue purified by means of column chromatography (n-hexane/EA=4:1).

Workup

  1. extractionextracted with EA
  2. dry with materialThe organic phase was dried over MgSO4
  3. customthe solvent removed under a vacuum
  4. customthe residue purified by means of column chromatography (n-hexane/EA=4:1)

Sources & evidence

ORD record
ord-3fc78759444741edba0e7cb4080aac46
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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