Ethylene Glycol → 2-[2-(Methylsulfanyl)ethyl]-1,3-dioxolane

HRID 1726541Notes

Reaction equation

HRID 1726541 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH:5]=[O:6].[CH2:7](O)[CH2:8][OH:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][S:2][CH2:3][CH2:4][CH:5]1[O:9][CH2:8][CH2:7][O:6]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 18635Methional

Product 1

HCID 203986662-[2-(Methylsulfanyl)ethyl]-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-(methylthio)propanal (5.2 g, 0.05 mol) and ethyleneglycol (3.4 g. 0.055 mol) in 100 mL of benzene was treated with 300 mg p-toluenesulfonic acid and heated at reflux for 4 hrs. The solution was cooled and decanted. Concentration and drying in vacuo provided the title compound as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ ppm:4.93 (1H, t, J=0.76 Hz) 3.74-4.03 (4H, m) 2.46-2.68 (2H, m) 2.08 (3H, s) 1.83-2.00 (2H, m).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hrs
  3. temperatureThe solution was cooled
  4. customdecanted
  5. concentrationConcentration
  6. customdrying in vacuo

Sources & evidence

ORD record
ord-5c290b9d492e4322817f70fcfa32374d
Source dataset
uspto-grants-2009_02
Patent number
US07491819B1

Reaction notes

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