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

HRID 250516

반응식

HRID 250516 반응식
[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]

참가 물질

5

반응물 2

HCID 174Ethylene GlycolHCID 671444-Propanoylanisole

생성물 1

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

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 1140Toluene용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-de95f840885a45589a53fa1041665680
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863313B2

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