Methyl Ethyl Ketone → HCID 11412560, compound

HRID 1816530Notes

Reaction equation

HRID 1816530 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:9](C)=O)[CH3:8].[C:12]1([CH3:19])[CH:17]=[CH:16][CH:15]=[C:14]([SH:18])[CH:13]=1.C(Br)C#C>O>[CH3:19][C:12]1[CH:13]=[C:14]([S:18][CH2:9][C:7]#[CH:8])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl Ketone3×HCID 7842Propargyl bromideHCID 79303-ThiocresolHCID 11430Potassium Carbonate

Product 1

HCID 11412560HCID 11412560, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A condenser, an internal thermometer, a mechanical stirrer and a dropping funnel were attached to a 5-L three-neck flask. Into the flask, were introduced 673 g of potassium carbonate and 1500 mL of methyl ethyl ketone. Into the dropping funnel, were introduced 500 g of m-toluenethiol and 200 mL of methyl ethyl ketone. Both were dropped in 10 minutes. The resulting mixture was intactly stirred at room temperature for 1 hour. The internal temperature was raised to 28° C. The three-neck flask was dipped in a water bath. Into the dropping funnel, were introduced 333 mL of propargyl bromide and 300 mL of methyl ethyl ketone. The dropping was then started. The dropping was carried out for 20 minutes while maintaining the internal temperature at about 55 to 65° C. by controlling the dropping. The stirring was intactly carried out under the water bath for 50 minutes. The resulting suspension of the reaction system was then directly filtered through a Buchner funnel, and the vessel and solids were washed with 900 mL of ethyl acetate. The obtained filtrate was subsequently vacuum concentrated. Further, 1500 mL of ethyl acetate, 2 L of water and 100 mL of 1 N HCl were added to separate an organic layer from an aqueous layer. The aqueous layer was extracted with 500 mL of ethyl acetate twice. The extract was washed with 1000 mL of a saturated brine twice and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated to provide 601.14 g of a crude substance (yield 92%, purity 88%). Only 300 g of the crude substance was distilled to obtain 239.68 g of 3-methyl-1-prop-2-ynylthiobenzene at 100 to 102° C./7 mmHg (recovery ratio 80%, purity>98%).

Workup

  1. customA condenser, an internal thermometer, a mechanical stirrer and a dropping funnel were attached to a 5-L three-neck flask
  2. additionBoth were dropped in 10 minutes
  3. temperatureThe internal temperature was raised to 28° C
  4. customThe three-neck flask was dipped in a water bath
  5. waitThe dropping was carried out for 20 minutes
  6. temperaturewhile maintaining the internal temperature at about 55 to 65° C.
  7. additionThe resulting suspension of the reaction system
  8. filtrationwas then directly filtered through a Buchner funnel
  9. washthe vessel and solids were washed with 900 mL of ethyl acetate
  10. concentrationconcentrated
  11. additionFurther, 1500 mL of ethyl acetate, 2 L of water and 100 mL of 1 N HCl were added
  12. customto separate an organic layer from an aqueous layer
  13. extractionThe aqueous layer was extracted with 500 mL of ethyl acetate twice
  14. washThe extract was washed with 1000 mL of a saturated brine twice
  15. dry with materialdried over anhydrous magnesium sulfate
  16. filtrationAfter filtration
  17. concentrationthe filtrate was concentrated
  18. customto provide 601.14 g of a crude substance (yield 92%, purity 88%)
  19. distillationOnly 300 g of the crude substance was distilled

Sources & evidence

ORD record
ord-93b3b423ba42405da514e83afd3fbf24
Source dataset
uspto-grants-2005_04
Patent number
US06884896B2

Reaction notes

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