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

HRID 1364551

Reaction equation

HRID 1364551 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]([OH:14])=[O:13].[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:15]([O-:17])=[O:16])[C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]([OH:14])=[O:13]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 744692,5-Dimethoxyphenylacetic acid

Product 1

HCID 123157582-(2,5-Dimethoxy-4-nitrophenyl)acetic acidYield 69%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of of 2,5-dimethoxyphenylacetic acid (1.00 g, 5.10 mmol) in 10 mL of acetic acid was added 6.5 mL of 1.0M HNO3 in acetic acid. The reaction was stirred at ambient temperature for 10 min, and diluted with 75 mL of water. The yellow precipitate was collected and washed with water (3×10 mL), then dried on the filter. Recrystallization from 20 mL of 2-propanol gave 846 mg (69%) of the titled compound as fine yellow crystals.

Workup

  1. customThe yellow precipitate was collected
  2. washwashed with water (3×10 mL)
  3. customdried on the filter
  4. customRecrystallization from 20 mL of 2-propanol

Sources & evidence

ORD record
ord-1b6198da01a148ad9b38abc99bb3f0bf
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Linked notes

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