Ethylene Glycol → HCID 13382128, compound

HRID 1251966Notes

Reaction equation

HRID 1251966 reaction equation
[CH:1](=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH2:6]([OH:9])[CH2:7][OH:8].[C:10]1([CH3:16])C=CC=CC=1.C1(C)C=CC(S(O)(=O)=[O:24])=CC=1>O>[OH:8][CH2:7][CH2:6][O:9][CH:3]([CH3:4])[CH2:2][CH:1]1[O:24][CH2:10][CH2:16][O:5]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 447466Crotonaldehyde

Product 1

HCID 13382128HCID 13382128, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A total of 35.0 g. (0.5 mole) of crotonaldehyde and 124 g. (2.0 mole of ethylene glycol were dissolved in 200 ml. of toluene and added to a 500 ml. round bottom flask equipped with magnetic stir bar, heating mantle, Dean-Starke trap, reflux condenser and nitrogen inlet. p-Toluene-sulfonic acid (0.6 g.-0.003 mole) was added to the mixture. The mixture was refluxed until the calculated amount of water (9.0 g.) was collected, cooled quickly in an ice bath to room temperature, and then dried and simultaneously neutralized with excess sodium carbonate. The solution was filtered and the solvent removed under vacuum (rotovap). The residual brown oil was subjected to high vacuum distillation The first fraction, collected between 55° and 80° C. at 0.5 mm./Hg, was primarily ethylene glycol. The second fraction, collected at between 80° and 90° C., was primarily the above dioxolane with a trace amount of ethylene glycol which can be removed by column chromatography (neutral alumina:ether/petroleum ether: 1/1). Yield was 50-60%.

Workup

  1. customround bottom flask equipped with magnetic stir bar
  2. temperatureheating mantle, Dean-Starke trap
  3. temperaturereflux condenser and nitrogen inlet
  4. customwas collected
  5. customdried
  6. filtrationThe solution was filtered
  7. customthe solvent removed under vacuum (rotovap)
  8. distillationThe residual brown oil was subjected to high vacuum distillation The first fraction
  9. customcollected between 55° and 80° C. at 0.5 mm
  10. customThe second fraction, collected at between 80° and 90° C.
  11. customcan be removed by column chromatography (neutral alumina:ether/petroleum ether: 1/1)

Sources & evidence

ORD record
ord-bdc30dc186a840ef997e285193cedf75
Source dataset
uspto-grants-1988_05
Patent number
US04741804

Reaction notes

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