Ethylene Glycol → 2-Pentyl-1,3-dioxolane

HRID 1723314Notes

Reaction equation

HRID 1723314 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:8](O)[CH2:9][OH:10].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH2:2]([CH:1]1[O:10][CH2:9][CH2:8][O:7]1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 81031-Hexanol

Product 1

HCID 770502-Pentyl-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

30 g (0.29 mole) of hexanol, 31 g (0.5 mol) of ethylene glycol, 100 mg of p-toluenesulfonic acid (p-Ts) in 100 ml of benzene are placed in 250 ml round-bottomed flask equipped with a Dean-Stark trap, a condenser and a mechanical stirrer. The mixture is heated to reflux until no more water has separated from the benzene phase. The mixture is then cooled to room temperature, washed with 100 ml of 5% sodium bicarbonate, 100 ml of saturated NaCl solution, and finally water. The solution is dried over sodium sulfate. After removing the solvent, the oil is fractionated. A yield of 19.6 g of colorless oil (46%) is obtaind nD20 =1.4554.

Workup

  1. customequipped with a Dean-Stark trap, a condenser and a mechanical stirrer
  2. temperatureThe mixture is heated
  3. customhas separated from the benzene phase
  4. washwashed with 100 ml of 5% sodium bicarbonate, 100 ml of saturated NaCl solution, and finally water
  5. dry with materialThe solution is dried over sodium sulfate
  6. customAfter removing the solvent

Sources & evidence

ORD record
ord-4278137c5fb74690991bda9b47b61e3c
Source dataset
uspto-grants-1989_08
Patent number
US04861764

Reaction notes

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