Nitric Acid → HCID 66889382, compound

HRID 253268Notes

Reaction equation

HRID 253268 reaction equation
S(=O)(=O)(O)O.[C:6]([O:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[C:13]([O:15][CH3:16])=[O:14])(=[O:8])[CH3:7].[N+:22]([O-])([OH:24])=[O:23]>>[C:6]([O:9][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([N+:22]([O-:24])=[O:23])[C:19]=1[O:20][CH3:21])[C:13]([O:15][CH3:16])=[O:14])(=[O:8])[CH3:7]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 66890465HCID 66890465, compound

Product 1

HCID 66889382HCID 66889382, compoundYield 88%

Conditions

Temperature
-5 °C

Procedure

A mixture of 90% nitric acid (40 mL) and concentrated sulfuric acid (8 mL) were cooled to −5° C. followed by portionwise addition of solid methyl 3-(acetyloxy)-4-(methyloxy)benzoate (25.9 g, 115 mmol.) over 25 minutes. After stirring for 5 minutes the solution was poured onto ice and the aqueous mixture was extracted once with dichloromethane. The organic solution was then washed with dilute aqueous sodium hydrogencarbonate (3×) then once with water and dried over anhydrous magnesium sulfate. Filtration and concentration followed by suspension of the solid residue in hexanes and filtration gave methyl 3-(acetyloxy)-4-(methyloxy)-5-nitrobenzoate (27.2 g, 88% yield) as a white solid on drying. 1H NMR (400 MHz, CDCl3): 8.38 (d, 1H), 7.99 (d, 1H), 4.00 (s, 3H), 3.95 (s, 3H), 2.40 (s, 3H).

Workup

  1. additionwas poured onto ice
  2. extractionthe aqueous mixture was extracted once with dichloromethane
  3. washThe organic solution was then washed with dilute aqueous sodium hydrogencarbonate (3×)
  4. dry with materialonce with water and dried over anhydrous magnesium sulfate
  5. filtrationFiltration and concentration
  6. additionfollowed by suspension of the solid residue in hexanes
  7. filtrationfiltration

Sources & evidence

ORD record
ord-92092a133a744e1096de8ac569c98e62
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

Loading…