Water → 3-Hydroxy-4-nitrophenyl acetate

HRID 337358Notes

Reaction equation

HRID 337358 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([O:14]C(=O)C)[CH:6]=1)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([OH:14])[CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 543636721,3-Benzenediol, 4-nitro-, 1,3-diacetate

Product 1

HCID 201396903-Hydroxy-4-nitrophenyl acetateYield 74%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-nitro-1,3-phenylene diacetate (1.0 g) in chloroform (25 mL) was added aluminium chloride (2.23 g) with ice-cooling under nitrogen atmosphere. The reaction mixture was warmed to room temperature and stirred for 3 h. Then to the reaction mixture was added water (100 mL) and extracted with methylene chloride (30 mL×2). The combined organic layer was washed with 1N hydrochloric acid (25 mL) and saturated brine (25 mL) successively, dried over anhydrous sodium sulfate and was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (20:1) to give the title compound (610 mg).

Workup

  1. temperaturecooling under nitrogen atmosphere
  2. extractionextracted with methylene chloride (30 mL×2)
  3. washThe combined organic layer was washed with 1N hydrochloric acid (25 mL) and saturated brine (25 mL) successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationwas concentrated under reduced pressure
  6. customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-f03343f9da814c78901e2d58476f63b9
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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