Nitric Acid → Phenol, 4-methoxy-3-nitro-, 1-acetate

HRID 1090697Notes

Reaction equation

HRID 1090697 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=CC(O)=[CH:5][CH:4]=1.[N+:10]([O-:13])(O)=[O:11].[C:14]([O:17][C:18](=[O:20])[CH3:19])(=O)[CH3:15]>C(O)(=O)C>[C:18]([O:17][C:14]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:8]([N+:10]([O-:13])=[O:11])[CH:15]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 90154-Methoxyphenol

Product 1

HCID 15676975Phenol, 4-methoxy-3-nitro-, 1-acetateYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

One mole of 4-methoxy-phenol in a mixture of 300 ml acetic anhydride and 300 ml acetic acid was refluxed for 12 hours. After cooling, 54 ml of nitric acid (1.3 equivalents, fuming nitric acid, d=1.52) was added dropwise at room temperature. The temperature rose to about 70° C. and nitrous vapors appeared. After completion of the addition the mixture was left under stirring for 2 hours to give 4-methoxy-3-nitrophenyl acetate as a precipitate. Isopropyl ether (300 ml) was added and the mixture was cooled to 0° C. The precipitated material was collected and dried, giving 190 g (yield=90%), m.p. 116° C.

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperatureAfter cooling
  3. customrose to about 70° C.
  4. additionAfter completion of the addition the mixture
  5. waitwas left

Sources & evidence

ORD record
ord-051d1802e388429bac00e376ee4e32c8
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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