Nitric Acid → (4,5-Dimethoxy-2-nitro-phenyl)-acetic acid

HRID 1380873Notes

Reaction equation

HRID 1380873 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:15]([O-])([OH:17])=[O:16]>>[CH3:10][O:9][C:8]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([CH2:11][C:12]([OH:14])=[O:13])=[C:6]([N+:15]([O-:17])=[O:16])[CH:7]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 7139(3,4-Dimethoxyphenyl)acetic acid

Product 1

HCID 270941(4,5-Dimethoxy-2-nitro-phenyl)-acetic acid

Conditions

Temperature
30 °C

Procedure

First, 3,4-dimethoxyphenylacetic acid (49.05 g, 0.25 mol) is added in batches to concentrated nitric acid (500 ml), with cooling, at 30° C. and stirred for a further 15 minutes with cooling. The reaction mixture is poured onto ice water (1.5 liters), the precipitate obtained is suction filtered, washed with ice water until neutral and dried. Yield: 56.4 g. Mp: 209°-211° C.

Workup

  1. temperaturewith cooling
  2. additionThe reaction mixture is poured onto ice water (1.5 liters)
  3. customthe precipitate obtained
  4. washwashed with ice water until neutral and
  5. customdried

Sources & evidence

ORD record
ord-8f4c9271b996408ca4ec1c5eff6ffd76
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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