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

HRID 250516

反応式

HRID 250516 の反応式
[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]

参加物

5

反応物 2

HCID 174Ethylene GlycolHCID 671444-Propanoylanisole

生成物 1

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

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 1140Toluene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-de95f840885a45589a53fa1041665680
出典データセット
uspto-grants-2011_01
特許番号
US07863313B2

関連ノート

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