Hydrochloric Acid → Dimethyl 2-(5-methoxy-2-nitrophenyl)malonate

HRID 491467Notes

Reaction equation

HRID 491467 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]([O:20][CH3:21])(=[O:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.C1(C)C=CC=CC=1>[CH3:18][O:17][C:15](=[O:16])[CH:14]([C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11])[C:13]([O:20][CH3:21])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 11430Potassium CarbonateHCID 5656543-Fluoro-4-nitroanisole

Product 1

HCID 68979054Dimethyl 2-(5-methoxy-2-nitrophenyl)malonate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-fluoro-4-methoxy-1-nitro-benzene (84.1 g, 0.49 mol) and dimethyl malonate (129.9 g, 0.98 mol) in DMF (490 ml), potassium carbonate (135.9 g, 0.98 mol) is added at ambient temperature. The reaction mixture is stirred at 70 C.° for 12 h. The reaction mixture is added to toluene (393 ml) and 12 N HCl (123 ml) and extracted with ethyl acetate. The combined extracts are washed with H2O and brine, dried over sodium sulfate and evaporated down to give 2-(5-methoxy-2-nitro-phenyl)-malonic acid dimethyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts are washed with H2O and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated down

Sources & evidence

ORD record
ord-a27467c55a434b6db7511b0013fb2dcd
Source dataset
uspto-grants-2009_05
Patent number
US07531546B2

Reaction notes

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