Ethylene Glycol → HCID 19986110, compound

HRID 974692Notes

Reaction equation

HRID 974692 reaction equation
[O:1]=[C:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:24](O)[CH2:25][OH:26].O>C1(C)C=CC=CC=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>[CH2:24]1[CH2:25][O:26][C:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[O:1]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 112885Octadecanoic acid, 3-oxo-, ethyl ester

Product 1

HCID 19986110HCID 19986110, compoundYield 61.4%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 1140TolueneSolvent

Procedure

26(a) A solution of 42.57 g of ethyl 3-oxostearate (prepared as described in Preparation 25). 9.71 g of ethylene glycol and 1 g of camphorsulfonic acid in 200 ml of toluene was heated under reflux for 24 hours, and the water produced was removed through a side arm attached to a water separator. The mixture was allowed to cool, and then washed, in turn, with a saturated aqueous solution of sodium bicarbonate and with water. It was then dried and concentrated by evaporation under reduced pressure, to give 29.66 g of crude ethyl 3,3-ethylenedioxystearate.

Workup

  1. temperatureunder reflux for 24 hours
  2. customwas removed through a side arm
  3. temperatureto cool
  4. washwashed, in turn, with a saturated aqueous solution of sodium bicarbonate and with water
  5. customIt was then dried
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-82ec68544c254b9e97d3ef92f8c47f1f
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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