p-Toluenesulfonic acid → HCID 20143886, compound

HRID 649352Notes

Reaction equation

HRID 649352 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH:9]=[CH2:10].[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][CH2:5][CH2:6][S:7][CH2:8][CH:9]=[CH2:10])[CH:13]([CH3:14])[CH3:12]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6560IsobutanolHCID 20143887HCID 20143887, compound

Product 1

HCID 20143886HCID 20143886, compound

Procedure

Into a 25 cc micro flask equipped with spin bar, hot plate (having built in magnetic stirrer), thermometer and reflux condenser are placed 5 grams (0.2874 moles) methyl-4-(allylthio)butyrate; 8.5 grams (0.1149 moles) of isobutanol and 0.05 grams of para-toluene sulfonic acid. The reaction mass is heated to reflux and maintained at reflux for a period of 14.33 hours. At the end of the refluxing period, the reaction mass is cooled to room temperature and charged to a distillation flask and distilled on a micro Vigreux column yielding the following fractions:

Workup

  1. customInto a 25 cc micro flask equipped with spin bar
  2. temperaturehot plate (having built in magnetic stirrer), thermometer and reflux condenser
  3. temperatureThe reaction mass is heated
  4. temperatureto reflux
  5. temperaturemaintained
  6. temperatureat reflux for a period of 14.33 hours
  7. additioncharged to a distillation flask
  8. distillationdistilled on a micro Vigreux column
  9. customyielding the following fractions

Sources & evidence

ORD record
ord-552388fc3b364b189397002f00aee6be
Source dataset
uspto-grants-1988_04
Patent number
US04739105

Reaction notes

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