Dimethylformamide → Methyl 3-isopropoxy-4-nitrobenzoate

HRID 1676531Notes

Reaction equation

HRID 1676531 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([OH:13])[CH:5]=1.I[CH:16]([CH3:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][CH:16]([CH3:18])[CH3:17])[CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 21187964Methyl 3-isopropoxy-4-nitrobenzoateYield 67.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g (10 mmole) of 3-hydroxy-4-nitro-benzoic acid methyl ester, 1.32 mL (13 mmole) of 2-iodopropane, 6.6 g (20 mole) of cesium carbonate and 60 mL of dimethylformamide was heated at 85 degrees overnight. The mixture was cooled, diluted with water and extracted twice with ethyl acetate. The combined organic layers were washed three times with sodium carbonate, three times with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with ethyl acetate-hexane (gradient, 100:0-70:30) gave 1.62 g of 3-isopropoxy-4-nitro-benzoic acid methyl ester as a yellow liquid.

Workup

  1. temperaturewas heated at 85 degrees overnight
  2. temperatureThe mixture was cooled
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layers were washed three times with sodium carbonate, three times with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography
  9. washeluting with ethyl acetate-hexane (gradient, 100:0-70:30)

Sources & evidence

ORD record
ord-f6e36f82571746bdb865fb023ba0a387
Source dataset
uspto-grants-2011_08
Patent number
US08003785B2

Reaction notes

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