Hydrochloric Acid → 6-Chloro-5-nitro-3H-isobenzofuran-1-one

HRID 1739837Notes

Reaction equation

HRID 1739837 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([Cl:17])=[CH:10][C:7]=1C#N)(=[O:3])C.C1COCC1.[OH-].[Na+].Cl>CO>[Cl:17][C:11]1[CH:10]=[C:7]2[C:6]([CH2:5][O:4][C:1]2=[O:3])=[CH:13][C:12]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 154289162-Acetoxymethyl-5-chloro-4-nitrobenzonitrile

Product 1

HCID 154289176-Chloro-5-nitro-3H-isobenzofuran-1-oneYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-acetoxymethyl-5-chloro-4-nitrobenzonitrile (19.5 g, 77 mmol) in MeOH:THF (600 mL, 2:1) was added a solution of 1M aqueous NaOH (100 mL, 100 mmol). After stirring at room temperature for 30 min. TLC showed no starting material remaining. The mixture was acidified with 6M aqueous HCl (100 mL, 0.6 mol), heated at 60° C. for 1 h, cooled to room temperature and stirred for 6 h. Volatile solvents were evaporated in vacuo. The residue was suspended in H2O and filtered. The solid collected was washed with H2O and dried under vacuum to give the title compound (14.5 g, 88%) as an orange-yellow solid. 1H NMR (CDCl3): δ 8.11 (s, 1H), 7.92 (s, 1H), 5.40 (s, 2H).

Workup

  1. temperatureheated at 60° C. for 1 h
  2. temperaturecooled to room temperature
  3. stirringstirred for 6 h
  4. customVolatile solvents were evaporated in vacuo
  5. filtrationfiltered
  6. customThe solid collected
  7. washwas washed with H2O
  8. customdried under vacuum

Sources & evidence

ORD record
ord-b9ec84dcafdd425db2fdb1c71d0da373
Source dataset
uspto-grants-1999_10
Patent number
US05968958

Reaction notes

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