Nitric Acid → Methyl 2-(3-nitro-4-hydroxyphenyl)propionate

HRID 328169Notes

Reaction equation

HRID 328169 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15]>C(O)(=O)C>[N+:14]([C:7]1[CH:6]=[C:5]([CH:8]([CH3:13])[C:9]([O:11][CH3:12])=[O:10])[CH:4]=[CH:3][C:2]=1[OH:1])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 12549710Methyl 2-(4-hydroxyphenyl)propanoate

Product 1

HCID 12872610Methyl 2-(3-nitro-4-hydroxyphenyl)propionate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a mixture of 18ml of nitric acid and 30ml of acetic acid 2.76g of methyl 2-(4-hydroxyphenyl)propionate was stirred at -10° to -20° C for 4 hours. The reaction mixture was poured into ice water and extracted with chloroform. The extract was washed with a sodium hydrogen carbonate solution and water and dried over magnesium sulfate. The chloroform was distilled off to give the desired compound in a yield of 2.35g (69%). The physical data of this compound coincided with those of the compound as described above.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with a sodium hydrogen carbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. distillationThe chloroform was distilled off

Sources & evidence

ORD record
ord-937cac51896e418286af13e5cc3938e3
Source dataset
uspto-grants-1977_04
Patent number
US04016193

Reaction notes

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