Dimethyl 2-(4-chloro-2-nitrophenyl)malonate → Methyl 2-(4-chloro-2-nitrophenyl)acetate

HRID 1827450Notes

Reaction equation

HRID 1827450 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])C(OC)=O>O.CN1C(=O)CCC1>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 1

HCID 2727544Dimethyl 2-(4-chloro-2-nitrophenyl)malonate

Product 1

HCID 10944246Methyl 2-(4-chloro-2-nitrophenyl)acetateYield 102.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-(4-Chloro-2-nitro-phenyl)-malonic acid dimethyl ester (195 g, 679.4 mmol) in water (100 mL) and NMP (1000 mL) was heated to reflux for 3.5 hours. The solvent was removed by rotary evaporation to an oil. The oil was dissolved in EtOAc, and then washed with water (5×300 mL). The aqueous layer was then extracted with EtOAc (4×300 mL). The organic was washed with water. The organic layers were combined and dried over MgSO4. After removing the solids by filtration, the solvent was evaporated to yield the desired product as a orange/brown solid (160.0 g, 95%).

Workup

  1. temperatureto reflux for 3.5 hours
  2. customThe solvent was removed by rotary evaporation to an oil
  3. dissolutionThe oil was dissolved in EtOAc
  4. washwashed with water (5×300 mL)
  5. extractionThe aqueous layer was then extracted with EtOAc (4×300 mL)
  6. washThe organic was washed with water
  7. dry with materialdried over MgSO4
  8. customAfter removing the solids
  9. filtrationby filtration
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-106b3696d95248948686785afde073a1
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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