Ethylene Glycol → 2-(Furan-3-yl)-1,3-dioxolane

HRID 1713015Notes

Reaction equation

HRID 1713015 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]=[O:7])=[CH:2]1.[CH2:8](O)[CH2:9][OH:10].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[O:1]1[CH:5]=[CH:4][C:3]([CH:6]2[O:10][CH2:9][CH2:8][O:7]2)=[CH:2]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 103513-Furaldehyde

Product 1

HCID 143269962-(Furan-3-yl)-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

As depicted in Scheme 13 above, a mixture of furan-3-carbaldehyde (1.20 mol), ethylene glycol (1.32 mol), p-toluenesulfonic acid (4.6 grams, 0.024 mol) and benzene (100 ml) is heated to reflux for 19 hours in a 500 ml round-bottomed flask fitted with a Dean-Stark trap, while water are removed from the mixture by azeotropic distillation. Once water ceases to condense, the reaction mixture is washed with saturated sodium bicarbonate (NaHCO3, 200 ml). The combined organic phase is washed with water (100 ml) and saturated sodium chloride (NaCl, 100 ml), dried over MgSO4, and then concentrated a rotary evaporator. The residual paste is purified by distillation at 80° C. and 10 Torr (1333 pascals).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 19 hours in a 500 ml round-bottomed flask
  3. customare removed from the mixture by azeotropic distillation
  4. customOnce water ceases to condense
  5. washthe reaction mixture is washed with saturated sodium bicarbonate (NaHCO3, 200 ml)
  6. washThe combined organic phase is washed with water (100 ml) and saturated sodium chloride (NaCl, 100 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customa rotary evaporator
  10. distillationThe residual paste is purified by distillation at 80° C.

Sources & evidence

ORD record
ord-c0ba14c527a1497e9828e2b80d621f18
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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