Nitric Acid → HCID 22272710, compound

HRID 1064835Notes

Reaction equation

HRID 1064835 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[CH3:12][O:13][CH2:14][C:15]1[C:20]([CH2:21][O:22][CH3:23])=[CH:19][CH:18]=[CH:17][C:16]=1[OH:24].COCC1C(COC)=C([N+]([O-])=O)C=CC=1O>C(#N)C.O>[CH3:12][O:13][CH2:14][C:15]1[C:20]([CH2:21][O:22][CH3:23])=[CH:19][CH:18]=[C:17]([N+:8]([O-:11])=[O:9])[C:16]=1[OH:24]

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 22272635HCID 22272635, compoundHCID 22272686HCID 22272686, compound

Product 1

HCID 22272710HCID 22272710, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Acetyl nitrate obtained by mixing acetic anhydride (306 mg, 3.0 mmol) with fuming nitric acid (189 mg, 3.0 mmol) at 0° C. was dropped into a solution of 2,3-bis(methoxymethyl)phenol (483 mg, 2.65 mmol) in acetonitrile (5 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 to provide a 2:1 mixture (329 mg; yield 54%) of 2,3-bis(methoxymethyl)-6-nitrophenol and 2,3-bis(methoxymethyl)-4-nitrophenol as 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-f4cdfe19767b449b934921404d6e2df1
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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