Nitric Acid → Dimethyl 3-hydroxy-4-nitrophthalate

HRID 1064831Notes

Reaction equation

HRID 1064831 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[OH:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:14]=1[C:23]([O:25][CH3:26])=[O:24]>C(#N)C.O>[OH:12][C:13]1[C:22]([N+:8]([O-:11])=[O:9])=[CH:21][CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:14]=1[C:23]([O:25][CH3:26])=[O:24]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 12223651Dimethyl 3-hydroxyphthalate

Product 1

HCID 22272660Dimethyl 3-hydroxy-4-nitrophthalateYield 94.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Acetyl nitrate obtained by mixing acetic anhydride (3.6 g, 36 mmol) with fuming nitric acid (2.16 g, 36 mmol) at 0° C. was dropped into a solution of dimethyl 3-hydroxyphthalate (3.8 g, 18 mmol) in acetonitrile (60 ml) at 0° C. followed by stirring for 40 minutes. The reaction solution was diluted with water and extracted with ether. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom. A 3:2 mixture (4.34 g; yield 94%) of dimethyl 3-hydroxy-4-nitrophthalate and dimethyl 3-hydroxy-6-nitrophthalatewas obtained as a yellow solid. This was used in the next reaction without separation and purification.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with water
  3. dry with materiala saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-94082a8a559745478ed853fce0196cd3
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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