p-Toluenesulfonic acid → HCID 20143892, compound

HRID 649350Notes

Reaction equation

HRID 649350 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH:5]([S:7][CH2:8][CH2:9][CH3:10])[CH3:6].[CH2:12](O)[CH:13](C)[CH3:14].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([O:2][C:3](=[O:11])[CH2:4][CH:5]([S:7][CH2:8][CH2:9][CH3:10])[CH3:6])[CH:13]([CH3:14])[CH3:12]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6560IsobutanolHCID 20143884HCID 20143884, compound

Product 1

HCID 20143892HCID 20143892, compound

Procedure

Into a 25 cc micro flask equipped with spin bar, hot plate (equipped with magnetic stirrer), reflux condenser and thermometer are placed 5 grams (0.0284 moles) of methyl-3-(propylthio)butyrate; 8.4 grams (0.1136 moles) of isobutyl alcohol and 0.05 grams of para-toluene sulfonic acid. With stirring, the reaction mass is heated to reflux and refluxed for a period of 14 hours. At the end of the 14 hour period, the reaction mass is cooled and distilled on a micro Vigreux column yielding the following fractions:

Workup

  1. customInto a 25 cc micro flask equipped with spin bar
  2. customhot plate (equipped with magnetic stirrer)
  3. temperaturereflux condenser
  4. temperaturethe reaction mass is heated
  5. temperatureto reflux
  6. temperaturerefluxed for a period of 14 hours
  7. temperatureAt the end of the 14 hour period, the reaction mass is cooled
  8. distillationdistilled on a micro Vigreux column
  9. customyielding the following fractions

Sources & evidence

ORD record
ord-9967913605a44d3bbc432f861c990c34
Source dataset
uspto-grants-1988_04
Patent number
US04739105

Reaction notes

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