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

HRID 1108710Notes

Reaction equation

HRID 1108710 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>C(O)(=O)C.O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][C:7]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of methyl 4-hydroxyphenylacetate (10.0 g) in acetic acid (55 ml) was added nitric acid (22.1 ml) at 0° C. The reaction mixture was stirred at 0° C. for 2 hours. After warmed to 20° C., the reaction mixture was diluted with water (200 ml) and precipitated crystals were collected. The crystals were dissolved in chloroform, and the solution was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from a mixture of chloroform and hexane to give methyl 4-hydroxy-3-nitrophenylacetate (9.3 g) as yellow crystals.

Workup

  1. temperatureAfter warmed to 20° C.
  2. customprecipitated crystals
  3. customwere collected
  4. dissolutionThe crystals were dissolved in chloroform
  5. washthe solution was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was recrystallized from a mixture of chloroform and hexane

Sources & evidence

ORD record
ord-e7d0ff0f3944429d801b65954dd41cf7
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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