Allyl Mercaptan → HCID 20143887, compound

HRID 1249337Notes

Reaction equation

HRID 1249337 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][CH2:5][CH2:6]Cl.C[O-].[Na+].[CH2:12]([SH:15])[CH:13]=[CH2:14]>O>[CH3:1][O:2][C:3](=[O:8])[CH2:4][CH2:5][CH2:6][S:15][CH2:12][CH:13]=[CH2:14]

Participants

5

Reactant 3

HCID 13367Allyl Mercaptan3×HCID 76612Butanoic acid, 4-chloro-, methyl ester3×HCID 10942334Sodium Methoxide3×

Product 1

HCID 20143887HCID 20143887, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 1 liter flask equipped with cooling bath, thermometer, reflux condenser and addition funnel as well as electric stirrer is placed 68.2 grams of methyl-4-chlorobutyrate. The methyl-4-chlorobutyrate is cooled to 20° C. The mixture of sodium methoxide and allyl mercaptan is added to the addition funnel. Over a period of 0.5 hours while maintaining the pot temperature at 20°-30° C., the mixture of allyl mercaptan and sodium methoxide is added slowly to the methyl-4-chlorobutyrate with stirring. The reaction is exothermic and requires slight cooling. At the end of the addition of the mixture of allyl mercaptan and sodium methoxide, the reaction mass is stirred for 1 hour and the temperature of the reaction mass is permitted to rise to 38° C. 500 ml water are then added to the reaction mass and the reaction mass is transferred to a separatory funnel. The reaction mass is then extracted with three 50 ml portions of methylene dichloride and dried over anhydrous sodium sulfate and filtered. The reaction mass is then distilled on a micro Vigreux column yielding the following fractions:

Workup

  1. customInto a 1 liter flask equipped
  2. temperaturewith cooling bath
  3. temperaturethermometer, reflux
  4. additioncondenser and addition funnel as well as electric stirrer
  5. additionis added to the addition funnel
  6. temperatureOver a period of 0.5 hours while maintaining the pot temperature at 20°-30° C.
  7. stirringthe reaction mass is stirred for 1 hour
  8. customto rise to 38° C
  9. customthe reaction mass is transferred to a separatory funnel
  10. extractionThe reaction mass is then extracted with three 50 ml portions of methylene dichloride
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. distillationThe reaction mass is then distilled on a micro Vigreux column
  14. customyielding the following fractions

Sources & evidence

ORD record
ord-687bad3f8cff4a5790dc970a3e44c3a7
Source dataset
uspto-grants-1986_12
Patent number
US04631194

Reaction notes

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