Water → (1,3-Diethylacetonyl)(1,3-diisopropylacetonyl)sulfide

HRID 972904Notes

Reaction equation

HRID 972904 reaction equation
O.C[O-].[Na+].[SH:5][CH:6]([C:10](=[O:15])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH:7]([CH3:9])[CH3:8].Cl[CH:17]([C:20](=[O:24])[CH2:21][CH2:22][CH3:23])[CH2:18][CH3:19]>CO>[CH:7]([CH:6]([S:5][CH:17]([CH2:18][CH3:19])[C:20]([CH2:21][CH2:22][CH3:23])=[O:24])[C:10]([CH2:11][CH:12]([CH3:14])[CH3:13])=[O:15])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 1085444-Heptanone, 3-chloro-HCID 10942334Sodium Methoxide2×HCID 205190993-Mercapto-2,6-dimethyl-4-heptanone

Product 1

HCID 22150014(1,3-Diethylacetonyl)(1,3-diisopropylacetonyl)sulfide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Into a 50 ml, round bottom, three-necked flask equipped with magnetic stirrer, pot thermometer, "Y" tube, nitrogen inlet tube, reflux condenser with cotton plug, and water bath is placed a solution of 0.65 grams (0.012 moles) of sodium methoxide dissolved in 10 ml anhydrous methanol. While maintaining the temperature of the reaction mass at 24°-27° C., a solution of 2.1 grams of 3-mercapto-2,6-dimethyl-4-heptanone dissolved in 12 ml anhydrous methanol is added to the sodium methoxide solution. 1.78 grams of 3-chloro-4-heptanone is then added to the reaction mass with stirring over a period of 2 minutes, the reaction mass temperature rising to 38° C. Two ml anhydrous methanol used as rinse is then added to the reaction mass, and with stirring the reaction mass temperature cools to 25° C. The reaction mass is continued to be stirred at 25° C. for a period of 5 hours. At this point 25 ml distilled water is added, and the resulting solid dissolves. The oil phase is extracted with three 15 ml portions of methylene chloride, and the extracts are combined and washed with one 10 ml portion of water. The extracts are then dried over anhydrous sodium sulfate and gravity filtered and concentrated on a rotary evaporator using water aspirator vacuum to a weight of 3.20 grams (yellow oil). GLC analysis (8 feet × 1/4 inches SE-30 column), NMR, IR and mass spectral analyses of GLC isolated material yield the information that the resulting product is 85% pure and has the structure: ##STR60##

Workup

  1. customInto a 50 ml, round bottom, three-necked flask equipped with magnetic stirrer
  2. temperatureWhile maintaining the temperature of the reaction mass at 24°-27° C.
  3. customrising to 38° C
  4. washas rinse
  5. additionis then added to the reaction mass
  6. stirringwith stirring the reaction mass temperature
  7. customcools to 25° C
  8. stirringto be stirred at 25° C. for a period of 5 hours
  9. distillationAt this point 25 ml distilled water
  10. additionis added
  11. dissolutionthe resulting solid dissolves
  12. extractionThe oil phase is extracted with three 15 ml portions of methylene chloride
  13. washwashed with one 10 ml portion of water
  14. dry with materialThe extracts are then dried over anhydrous sodium sulfate and gravity
  15. filtrationfiltered
  16. concentrationconcentrated on a rotary evaporator
  17. customGLC analysis (8 feet × 1/4 inches SE-30 column), NMR, IR and mass spectral analyses of GLC isolated material
  18. customyield the information that the resulting product

Sources & evidence

ORD record
ord-47e1623fc40f4315a1eaac5d1a5fb800
Source dataset
uspto-grants-1977_10
Patent number
US04053655

Reaction notes

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