Nitric Acid → 4-Acetoxy-3,5-dimethoxy-2-nitrobenzoic Acid

HRID 1830959Notes

Reaction equation

HRID 1830959 reaction equation
[N+:1]([O-:4])(O)=[O:2].C([O:8][C:9](=[O:21])[C:10]1[CH:20]=[C:17]([O:18][CH3:19])[C:15]([OH:16])=[C:12]([O:13][CH3:14])[CH:11]=1)(=O)C.[C:22](OC(=O)C)(=[O:24])[CH3:23]>>[C:22]([O:16][C:15]1[C:12]([O:13][CH3:14])=[CH:11][C:10]([C:9]([OH:8])=[O:21])=[C:20]([N+:1]([O-:4])=[O:2])[C:17]=1[O:18][CH3:19])(=[O:24])[CH3:23]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 86760109O-Acetylsyringic Acid

Product 1

HCID 220466704-Acetoxy-3,5-dimethoxy-2-nitrobenzoic Acid

Procedure

Fuming nitric acid (5.2 mL) was added, carefully, to a solution of o-acetylsyringic acid 82 (11.1 g, 46.2 mmol) in acetic anhydride (33 g, mmol) at 5° C. and the reaction mixture was then allowed to stir for 3 hours at room temperature. The reaction mixture was poured over ice (300 mL) and the yellow precipitate was collected by filtration, washed with water (3×100 mL) and dried in vacuo to afford the product as a pale yellow solid (12.4 g). H1 NMR (270 MHz, CDCl3) δ7.37 (s, 1H), 3.92 (s, 3H), 3.90 (s, 3H), 2.39 (s, 3H).

Workup

  1. customat 5° C.
  2. filtrationthe yellow precipitate was collected by filtration
  3. washwashed with water (3×100 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-101bbb06db854728a44e6981be19efc6
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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