Acetone → HCID 118071468, compound

HRID 1775436Notes

Reaction equation

HRID 1775436 reaction equation
C([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([Cl:13])[C:5]=1[OH:14])C=C.[CH3:15][C:16]([CH3:18])=[O:17].[OH2:19]>C(O)(C)(C)C.C[N+]1([O-])CCOCC1.[Os](=O)(=O)(=O)=O>[Cl:13][C:6]1[C:5]([OH:14])=[C:4]([CH2:15][CH:16]([OH:17])[CH2:18][OH:19])[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=1

Participants

7

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 118071495HCID 118071495, compound

Product 1

HCID 118071468HCID 118071468, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 82029Methyl morpholine oxideSolvent

Procedure

To a mixture of 2-allyl-6-chloro-4-nitrophenol (30.0 g), acetone (270 mL), and water (30.0 mL) were added a 2.5 wt % osmium (VIII) oxide solution in tert-butanol (10.0 mL) and 4-methylmorpholin-4-oxide (18.1 g), followed by stirring at room temperature for 41 hours. The reaction mixture was concentrated under reduced pressure, acidified with 1 M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration, the filtrate was concentrated under reduced pressure, and the obtained solid was washed with a mixed solvent of chloroform and hexane to obtain 3-(3-chloro-2-hydroxy-5-nitrophenyl)propane-1,2-diol (20.8 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble materials were separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washthe obtained solid was washed with a mixed solvent of chloroform and hexane

Sources & evidence

ORD record
ord-8cdd44dac73b43968aa54dd40c852bea
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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