Ethanol → 3-(2-Iodo-6-nitro-phenyl)-2-oxo-propionic acid

HRID 2191519Notes

Reaction equation

HRID 2191519 reaction equation
[O-]CC.[Na+].[I:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH3:15].C(O)C.[C:19](OCC)(=[O:25])[C:20]([O:22]CC)=[O:21]>O>[I:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[C:7]=1[CH2:15][C:19](=[O:25])[C:20]([OH:22])=[O:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 115362581-Iodo-2-methyl-3-nitrobenzene

Product 1

HCID 592500863-(2-Iodo-6-nitro-phenyl)-2-oxo-propionic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Sodium ethoxide solution (35 ml, 44 mmol) in an ice-water bath was added dropwise with a solution of 1-iodo-2-methyl-3-nitro-benzene 74b in ethanol (35 ml, 40 mmol) under an argon atmosphere. Upon completion of the addition, the reaction mixture was stirred until substantial brown precipitates were formed, and added with diethyl oxalate (6 ml, 44 mmol) in one portion. The reaction mixture was refluxed at 100° C. in an oil bath for 0.5 hour, added with water (70 ml) and refluxed for another 1 hour. The reaction mixture was concentrated under reduced pressure to evaporate ethanol, washed with ethyl acetate (50 ml) under base condition, adjusted to pH 3 with hydrochloric acid (1M), and extracted with ethyl acetate (30 ml×3). The combined organic extracts were washed with saturated brine (30 ml), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 3-(2-iodo-6-nitro-phenyl)-2-oxo-propionic acid 74c (2.94 g) as a brown oil to be used directly in the next step.

Workup

  1. additionUpon completion of the addition
  2. custombrown precipitates
  3. customwere formed
  4. temperaturerefluxed for another 1 hour
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customto evaporate ethanol
  7. washwashed with ethyl acetate (50 ml) under base condition
  8. extractionextracted with ethyl acetate (30 ml×3)
  9. washThe combined organic extracts were washed with saturated brine (30 ml)
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ece1f7ac453743f6a2599f29c3c1918d
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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