Sodium Hydroxide → HCID 18329114, compound

HRID 1249906Notes

Reaction equation

HRID 1249906 reaction equation
[OH-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH:9]1([C:12](=[O:22])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH2:11][CH2:10]1>CS(C)=O>[CH:9]1([C:12]([CH:13]2[CH2:4][CH:14]2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[O:22])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 54340753HCID 54340753, compound

Product 1

HCID 18329114HCID 18329114, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a 500 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet, thermometer and addition funnel was charged 20 g (0.5 moles) of powdered sodium hydroxide, 110 (0.5 moles) of trimethyl sulfoxonium iodide, and 200 mls of anhydrous DMSO. The mixture was then stirred at ambient temperature for 30 minutes. The mixture was then cooled to 15° C., and a solution of 1-cyclopropyl-3-(3-hydroxyphenyl)-2-propene-1-one (47 g, 0.25 moles) was added dropwise in 50 mls of DMSO. The reaction was stirred for 2 hours at 10-15° C., then allowed to warm to ambient temperature, and stirred for an additional 16 hours. The reaction mixture was the quenched with 200 mls of 0.1 N HCl, and extracted with 3×100 mls of ethyl ether. The combined ether extracts were washed successively with 2×100 mls of water, and 100 mls of saturated aqueous sodium chloride solution. The ether extract was then dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure with a rotary evaporator at 45° C. to afford 32 g of the title compound, 2-(3-hydroxyphenyl)cyclopropyl cyclopropyl ketone, as a thick amber oil that crystallized upon standing in a 64% isolated yield.

Workup

  1. customTo a 500 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet
  2. additionthermometer and addition funnel
  3. temperatureThe mixture was then cooled to 15° C.
  4. stirringThe reaction was stirred for 2 hours at 10-15° C.
  5. temperatureto warm to ambient temperature
  6. stirringstirred for an additional 16 hours
  7. customquenched with 200 mls of 0.1 N HCl
  8. extractionextracted with 3×100 mls of ethyl ether
  9. washThe combined ether extracts were washed successively with 2×100 mls of water, and 100 mls of saturated aqueous sodium chloride solution
  10. extractionThe ether extract
  11. dry with materialwas then dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated to dryness under reduced pressure with a rotary evaporator at 45° C.

Sources & evidence

ORD record
ord-0bb1cba57f47409a9019d36f4697063e
Source dataset
uspto-grants-2002_01
Patent number
US06335367B1

Reaction notes

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