Sodium Hydroxide → HCID 12623953, compound

HRID 1952895Notes

Reaction equation

HRID 1952895 reaction equation
[OH-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[OH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:13]=[CH:14][CH:15]=1>CS(C)=O>[C:18]([CH:17]1[CH2:4][CH:16]1[C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([OH:9])[CH:11]=1)(=[O:19])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 317158HCID 317158, compound

Product 1

HCID 12623953HCID 12623953, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
15 °C

Procedure

To a 250 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet, thermometer and addition funnel was charged 0.71 g (0.0178 moles) of 60% sodium hydroxide (oil suspension) and 50 mls of anhydrous DMSO. With stirring, under a nitrogen atmosphere, the trimethysulfoxonium iodide (3.9 g, 0.0178 moles) was added in one portion, and the reaction was stirred at ambient temperature for 30 minutes. The mixture was then cooled to 15° C., and a solution of 3-hydroxychalcone (2.0 g, 0.0089 moles) was added dropwide in 10 mls of DMSO. The reaction was stirred for 1 hour at 15° C., then allowed to warm to ambient temperature, and stirred for an additional 16 hours. The reaction mixture was the quenched with 100 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 2.1 g of the title compound, 2-benzoyl-1-(3-hydroxyphenyl)cyclopropane, as a thick yellow oil. 100% crude yield.

Workup

  1. customTo a 250 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet
  2. additionthermometer and addition funnel
  3. stirringthe reaction was stirred at ambient temperature for 30 minutes
  4. stirringThe reaction was stirred for 1 hour at 15° C.
  5. temperatureto warm to ambient temperature
  6. stirringstirred for an additional 16 hours
  7. customquenched with 100 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-213fda3c64044b7d92d11a6d1826211a
Source dataset
uspto-grants-2000_09
Patent number
US06114375

Reaction notes

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