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

HRID 268264Notes

Reaction equation

HRID 268264 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[N+:13]([O-])([OH:15])=[O:14]>CC(O)=O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([N+:13]([O-:15])=[O:14])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 709874-Methoxyphenyl acetate

Product 1

HCID 15676975Phenol, 4-methoxy-3-nitro-, 1-acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 270 g. (1.62 m.) of p-methoxyphenyl acetate (part A) and 772 ml. of HOAc was added dropwise 77.5 ml. of fuming HNO3 maintaining a temperature of 5° to 10°C. Stirring was continued for 60 minutes at 5° to 10°C following the addition, then the solution was poured into 6 liters of ice. The orange semi-solid was collected by filtration and washed with cold water. The crude product was recrystallized from 1000 ml. of ethanol to give 61 g., m.p. 93°-97°C.

Workup

  1. additionTo a mixture of 270 g
  2. customa temperature of 5° to 10°C
  3. additionthe addition
  4. filtrationThe orange semi-solid was collected by filtration
  5. washwashed with cold water
  6. customThe crude product was recrystallized from 1000 ml
  7. customof ethanol to give 61 g

Sources & evidence

ORD record
ord-c7f71e84442b488b87cade1ad7cfd357
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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