Water → HCID 19048059, compound

HRID 1616982Notes

Reaction equation

HRID 1616982 reaction equation
[N+]([O-])([O:3][CH2:4][C:5](=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([I:13])=[CH:9][CH:8]=1)=O.O.O.O.C([O-])(=O)C.[Na+].O>CS(C)=O>[I:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C:5](=[O:14])[CH:4]=[O:3])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665404Sodium Acetate TrihydrateHCID 66725062HCID 66725062, compound

Product 1

HCID 19048059HCID 19048059, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-(4-Iodophenyl)-2-oxopropyl nitrate (17) (450 mg) was dissolved in dimethylsulfoxide (20 mL) and to this was added sodium acetate trihydrate (211 mg, 1.55 mmol), and stirred for an hour at room temperature. To this was added water and the product was extracted with diethyl ether (×3). The organic layer was washed sequentially with water (×1), saturated aqueous solution of sodium bicarbonate (×1) and saturated brine (×1), and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to give 3-(4-iodophenyl)-2-oxopropanal (18) as an orange solid (346 mg, <1.26 mmol, <90.1%), which was used in the next reaction without further purification.

Workup

  1. extractionthe product was extracted with diethyl ether (×3)
  2. washThe organic layer was washed sequentially with water (×1), saturated aqueous solution of sodium bicarbonate (×1) and saturated brine (×1)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-276692a554334491878945c89d73cbcf
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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