Sodium Hydroxide → HCID 18329110, compound

HRID 1249907Notes

Reaction equation

HRID 1249907 reaction equation
[OH-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([C:15](=[O:25])[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>CS(C)=O>[CH2:9]([C:15]([CH:16]1[CH2:4][CH:17]1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=1)=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 324298HCID 324298, compound

Product 1

HCID 18329110HCID 18329110, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a 300 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet, thermometer and addition funnel was charged 0.3 g (0.0069 moles) of powdered sodium hydroxide, 1.5 g (0.0069 moles) of trimethyl sulfoxonium iodide, and 50 mls of anhydrous DMSO. The mixture was then stirred at ambient temperature for 1 hour. The mixture was then cooled to 15° C., and a solution of 1-n-hexyl-3-(3-hydroxyphenyl)-2-propene-1-one (0.8 g, 0.0069 moles) was added dropwise in 5 mls of DMSO. The reaction was stirred for 1 hour 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 0.64 g of the title compound, 2-(3-hydroxyphenyl)cyclopropyl n-hexyl ketone, as a thick yellow oil in a 76% isolated yield.

Workup

  1. customTo a 300 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 1 hour 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-8f6db76bd3c345b2ac202cbed8c58cc5
Source dataset
uspto-grants-2002_01
Patent number
US06335367B1

Reaction notes

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