Acetone → HCID 22416126, compound

HRID 1885908Notes

Reaction equation

HRID 1885908 reaction equation
[C:1]([C:9]1([CH3:12])[CH2:11][O:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:13][C:14]([CH3:16])=[O:15].B(F)(F)F.CCOCC.[OH-].[Na+]>O>[C:1]([C:9]1([CH3:12])[CH2:11][O:10][C:14]([CH3:16])([CH3:13])[O:15]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 180Acetone2×HCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 12694224(2-Methyloxiran-2-yl)(phenyl)methanone

Product 1

HCID 22416126HCID 22416126, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16.2 g (0.1 mol) of 2-benzoyl-2-methyloxirane (see Example 1) are dissolved in 35 g (0.6 mol) of acetone, and a solution of 1.42 g (0.01 mol) of boron trifluoride-etherate in 35 g (0.6 mol) of acetone is then added dropwise while the mixture is cooled by means of an ice bath. The mixture is then stirred for 2 hours at room temperature and is then heated under reflux for 5 hours. The reaction solution is cooled, rendered alkaline, with cooling, by means of 50 ml of saturated methanolic sodium hydroxide solution, and diluted with 200 ml of water. The product is extracted with ether. The ether solution is dried with potassium carbonate and concentrated. The residue is distilled in vacuo at 95° C. and 0.5° mbar. The distillate is purified by mediumpressure chromatography, a colourless oil being obtained.

Workup

  1. temperatureis cooled by means of an ice bath
  2. temperatureis then heated
  3. temperatureunder reflux for 5 hours
  4. temperatureThe reaction solution is cooled
  5. extractionThe product is extracted with ether
  6. dry with materialThe ether solution is dried with potassium carbonate
  7. concentrationconcentrated
  8. distillationThe residue is distilled in vacuo at 95° C. and 0.5° mbar
  9. distillationThe distillate is purified by mediumpressure chromatography
  10. customa colourless oil being obtained

Sources & evidence

ORD record
ord-b5b32350f6364271b30d72104f1c468f
Source dataset
uspto-grants-1992_09
Patent number
US05147901

Reaction notes

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