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

HRID 48147Notes

Reaction equation

HRID 48147 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7](=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1>C(O)(=O)C>[CH3:5][O:6][C:7](=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([N+:1]([O-:4])=[O:2])[CH:10]=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

Nitric acid (69% by weight, 16M, 20 ml) was added dropwise to a solution of methyl (4-hydroxyphenyl)acetate [from step 2] (50.0 g, 0.3 mole) in acetic acid (500 ml), maintaining the temperature of the reaction below 15° C. by external cooling. (An induction period was observed for this reaction.) Once gas chromatographic analysis had confirmed that the reaction was complete, the mixture was carefully quenched into water (21) with vigorous stirring. An emulsion formed which subsequently crystallised. After filtration, washing with water and drying, the desired product was obtained as a yellow powder.

Workup

  1. temperaturemaintaining
  2. customthe temperature of the reaction below 15° C. by external cooling
  3. custom(An induction period was observed for this reaction
  4. customthe mixture was carefully quenched into water (21) with vigorous stirring
  5. customAn emulsion formed which
  6. customsubsequently crystallised
  7. filtrationAfter filtration
  8. washwashing with water
  9. customdrying

Sources & evidence

ORD record
ord-f8385b9d524f4c36a1481cb004b3908d
Source dataset
uspto-grants-2004_03
Patent number
US06703347B2

Reaction notes

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