Dichloromethane → 1-Propanone, 2-chloro-1-[4-(phenylmethoxy)phenyl]-

HRID 2217789Notes

Reaction equation

HRID 2217789 reaction equation
C(Cl)[Cl:2].[CH2:4]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][CH3:20])=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.S(Cl)(Cl)(=O)=O>O>[CH2:4]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18](=[O:21])[CH:19]([Cl:2])[CH3:20])=[CH:16][CH:17]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 78246p-Benzyloxypropiophenone

Product 1

HCID 121191951-Propanone, 2-chloro-1-[4-(phenylmethoxy)phenyl]-Yield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a methylene chloride solution (20 mL) of 4.80 g (20 mmol) of p-(benzyloxy)propiophenone, 2.97 g (1.1 equivalents) of sulfuryl chloride was added at 15° C., followed by 16 hours of stirring. After 20 mL of water was added, methylene chloride was distilled off under a reduced pressure, and extraction was conducted by adding 40 mL of ethyl acetate. The organic layer was washed with 20 mL of a saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and subjected to distillation under a reduced pressure to remove the solvent. A colorless, oily substance (6.299 g) was thereby obtained. The oily substance was crystallized from 0.5 mL of ethyl acetate and 20 mL of hexane to obtain white crystals of 1-[4-(benzyloxy)phenyl]-2-chloro-1-propanone (4.3787 g, isolation yield: 75%).

Workup

  1. distillationmethylene chloride was distilled off under a reduced pressure, and extraction
  2. additionby adding 40 mL of ethyl acetate
  3. washThe organic layer was washed with 20 mL of a saturated sodium hydrogen carbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationsubjected to distillation under a reduced pressure
  6. customto remove the solvent
  7. customA colorless, oily substance (6.299 g) was thereby obtained
  8. customThe oily substance was crystallized from 0.5 mL of ethyl acetate and 20 mL of hexane

Sources & evidence

ORD record
ord-a417cceb62504998a4845dc7b111d11e
Source dataset
uspto-grants-2008_08
Patent number
US07408084B2

Reaction notes

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