Methanesulfonic Acid → HCID 86737145, compound

HRID 1856113Notes

Reaction equation

HRID 1856113 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:20]1(=[O:27])[O:26][C:24](=[O:25])[CH2:23][CH2:22][CH2:21]1.[CH3:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].CS(O)(=O)=O>O>[C:24]([O:26][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:1]/[CH:2]=[CH:3]\[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])(=[O:25])[CH2:23][CH2:22][CH2:21][C:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:27]

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 7940Glutaric anhydrideHCID 8900HeptaneHCID 5284499Oleyl Alcohol2×

Product 1

HCID 86737145HCID 86737145, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Dioleyl glutarate was synthesized by refluxing 421.2 grams (1.57 moles) oleyl alcohol, 85.6 grams (0.75 mole) glutaric anhydride, 204 grams (300 ml) heptane and 0.96 grams (0.01 mole) methane sulfonic acid under a nitrogen atmosphere for 5 hours in a 3-liter, 3-necked flask equipped with an air driven stirrer, thermometer, reflux condenser and heating mantle. Water produced in the reaction was removed in a Dean-Stark trap. The product solution was allowed to cool to 25° C. overnight with agitation and under a nitrogen atmosphere. Next, the product solution was diluted with 300 ml of hexane, washed with 2% aqueous sodium hydroxide and dried over molecular sieves. Most of the hydrocarbon solvent was removed by rotary evaporation using a water aspirator vacuum source. High vacuum stripping at a pressure of from 1.5 mm.Hg. to 2.0 mm.Hg. and a temperature of from 240° C. to 260° C. for 4 hours removed the last traces of solvent. Analysis indicates that the dioleyl glutarate produced contained 3.8% oleyl alcohol.

Workup

  1. customequipped with an air
  2. temperaturethermometer, reflux condenser
  3. temperatureheating mantle
  4. customwas removed in a Dean-Stark trap
  5. additionNext, the product solution was diluted with 300 ml of hexane
  6. washwashed with 2% aqueous sodium hydroxide
  7. customdried over molecular sieves
  8. customMost of the hydrocarbon solvent was removed by rotary evaporation
  9. customand a temperature of from 240° C. to 260° C. for 4 hours removed the last traces of solvent
  10. customproduced

Sources & evidence

ORD record
ord-9601aa72782e410c94d045e5353df9ad
Source dataset
uspto-grants-1980_08
Patent number
US04218331

Reaction notes

Loading…