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

HRID 1264617Notes

Reaction equation

HRID 1264617 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].O>C(O)(=O)C>[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 3

HCID 944Nitric AcidHCID 962WaterHCID 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 4-hydroxyphenylacetate (49.8 g, 0.3 mol) was dissolved in glacial acetic acid (500 ml) and the resultant solution was cooled to below 15° C. Concentrated nitric acid (40 ml) was added slowly and the reaction mixture was sired until completion and then poured onto a mixture of ice and water. The precipitated solid was filtered, washed with ice cold water and dried to give methyl 4-hydroxy-3-nitrophenylacetate (51.2 g) as a yellow solid.

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with ice cold water
  3. customdried

Sources & evidence

ORD record
ord-a9815a95378746dc9e2550107953cf17
Source dataset
uspto-grants-2003_04
Patent number
US06544989B2

Reaction notes

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