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

HRID 1090689Notes

Reaction equation

HRID 1090689 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)[CH3:19])(=[O:16])[CH3:15]>C(O)(=O)C>[N+:10]([C:8]1[CH:19]=[C:18]([O:17][C:14](=[O:16])[CH3:15])[CH:5]=[CH:4][C:3]=1[O:2][CH3:1])([O-:13])=[O:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 90154-Methoxyphenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-methoxy-phenol is acetylated by reflux in a mixture of acetic anhydride and acetic acid for a period of about 10 to 15 hours, preferably about 12 hours. The acetylated derivative is nitrated by contact with a slight molar excess of nitric acid at room temperature, with stirring for about 1 to 4 hours, preferably about 2 hours giving 2-nitro-4-acetyloxy-anisole. The 2-nitro-4-acetyloxy-anisole is hydrogenated to give the corresponding aniline of Formula 12.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-cf63d2d2960c45e5b2261a314f65a7ad
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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