Ethylene Glycol → 2-Methyl-2-(3-butenyl)-1,3-dioxolane

HRID 395896Notes

Reaction equation

HRID 395896 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][CH2:4][CH:5]=[CH2:6].[CH2:8](O)[CH2:9][OH:10].C1(C)C=CC=CC=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH3:1][C:2]1([CH2:3][CH2:4][CH:5]=[CH2:6])[O:10][CH2:9][CH2:8][O:7]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 1140TolueneHCID 79895-Hexene-2-one

Product 1

HCID 117686812-Methyl-2-(3-butenyl)-1,3-dioxolaneYield 46.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 962WaterSolvent2×

Procedure

In a 200 mL RB flask, 5-hexen-2-one (37.18 g, 0.3788 mol) was mixed with ethylene glycol (23.49 g, 0.3788 mol), 0.72 g p-toluenesulfonic acid monohydrate and 40 mL toluene. A graduated water collector and a reflux condenser were connected to the flask. The mixture was refluxed overnight. The reaction was completed as shown by the amount of water collected (ca. 7 mL). After evaporation of toluene, the mixture was distilled under reduced pressure to gave 25 g of pure product. 1H NMR(CDCl3): δ1.31(s, 3H, —CH3); 1.72(m, 2H, CH2═CHCH2CH2—); 2.13(m, 2H, CH2═CHCH2CH2—); 3.92(m, 4H, —OCH2CH2O—); 4.95(m, 2H, CH2═CH—); 5.80(m, 1H, CH2═CH—).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customcollected (ca. 7 mL)
  3. customAfter evaporation of toluene
  4. distillationthe mixture was distilled under reduced pressure

Sources & evidence

ORD record
ord-dd30dc34d27e434d9ef3d5e284dcece4
Source dataset
uspto-grants-2003_08
Patent number
US06605679B1

Reaction notes

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