Ethylene Glycol → 2-Ethyl-2-(4-methoxyphenyl)-1,3-dioxolane

HRID 250516

Reaction equation

HRID 250516 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.[CH2:13](O)[CH2:14][OH:15]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:10]([C:9]1([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:15][CH2:14][CH2:13][O:12]1)[CH3:11]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 671444-Propanoylanisole

Product 1

HCID 114131172-Ethyl-2-(4-methoxyphenyl)-1,3-dioxolaneYield 58.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4′-methoxypropiophenone (250.0 mg, 1.52 mmol) in toluene (20.0 mL) was added ethylene glycol (255.0 μL, 4.57 mmol) and p-toluenesulfonic acid monohydrate (13.0 mg, 0.04 mmol) and the reaction mixture refluxed overnight using a Dean-Stark apparatus. The reaction mixture was cooled to room temperature, then washed with saturated aqueous sodium bicarbonate solution followed by water. The toluene solution was then dried (MgSO4) and evaporated under reduced pressure to afford 2-ethyl-2-(4-methoxyphenyl)-1,3-dioxolane (16) as a yellow oil (184 mg, 58%). 1H nmr (CDCl3, 300 MHz) 0.76, t (6.6 Hz), CH3; 1.78, q (6.9 Hz), CH2; 3.65, m, CH2O, 3.73, s, 4′-OMe; 3.95, m, CH2O; 6.88, d (7.2 Hz), H3′,5′; 7.02, d, (7.5 Hz), H2′,6′. ESI (+ve) MS m/z 209 (M+H, 100%).

Workup

  1. temperaturethe reaction mixture refluxed overnight
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe toluene solution was then dried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-de95f840885a45589a53fa1041665680
Source dataset
uspto-grants-2011_01
Patent number
US07863313B2

Linked notes

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