Phthalide → 6-Nitrophthalide

HRID 1896945Notes

Reaction equation

HRID 1896945 reaction equation
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][O:2]1.[N+:11]([O-])([O-:13])=[O:12].[K+]>S(=O)(=O)(O)O>[N+:11]([C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][O:2][C:1]2=[O:10])=[CH:5][CH:6]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 6885PhthalideHCID 24434Potassium Nitrate

Product 1

HCID 2235846-Nitrophthalide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 2000 mL 3-necked round-bottom flask, was placed a solution of isobenzofuran-1(3H)-one (130 g, 970.15 mmol, 1.00 equiv) in sulfuric acid (200 mL). This was followed by the addition of a solution of potassium nitrate (196 g, 1.94 mol, 1.39 equiv) in sulfuric acid (600 mL) dropwise with stirring at 0° C. The reaction mixture was stirred overnight at room temperature. The solid was collected by filtration and washed with 5×800 mL of H2O. This resulted in 136 g (crude) of 6-nitroisobenzofuran-1(3H)-one as a white solid.

Workup

  1. customInto a 2000 mL 3-necked round-bottom flask, was placed
  2. stirringThe reaction mixture was stirred overnight at room temperature
  3. filtrationThe solid was collected by filtration
  4. washwashed with 5×800 mL of H2O
  5. customThis resulted in 136 g (crude) of 6-nitroisobenzofuran-1(3H)-one as a white solid

Sources & evidence

ORD record
ord-0fd249bbd80e4c199bf26bd448426ba0
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

Loading…