Dichloromethane methanol → Methyl 2-methoxy-4-nitrobenzeneacetate

HRID 858505Notes

Reaction equation

HRID 858505 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH2:12][C:13]([OH:15])=[O:14].CO.Cl[CH2:19]Cl>>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[CH2:12][C:13]([O:15][CH3:19])=[O:14]

Participants

3

Reactant 2

HCID 21226129Dichloromethane methanolHCID 21875535415912-52-6

Product 1

HCID 21875908Methyl 2-methoxy-4-nitrobenzeneacetate

Procedure

To a solution of 2-(2-methoxy-4-nitrophenyl)acetic acid (step 2, 1.2 g, 5.5 mmol) in methanol/dichloromethane (11 ml, 1/1) was added trimethylsillyldiazomethane (2 M, 5.6 ml, 11.8 mmol) and stirred for 10 min at room temperature. The mixture was quenched with saturated citric acid aqueous solution and the extracted with ethyl acetate (3×20 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated to give 1.2 g of title compound as orange solid.

Workup

  1. customThe mixture was quenched with saturated citric acid aqueous solution
  2. extractionthe extracted with ethyl acetate (3×20 ml)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d3c109d3838b4139af7f2aa2288cd3a8
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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