2-Chloroethanol → Benzoic acid, 4-(2-hydroxyethoxy)-, methyl ester

HRID 552574

反応式

HRID 552574 の反応式
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:13][CH2:14][OH:15].[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].ClC(O)C>C(Cl)Cl.O.C1COCC1>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:13][CH2:14][OH:15])=[CH:11][CH:10]=1

参加物

9

反応物 5

HCID 342-ChloroethanolHCID 4875Potassium Iodide2 回HCID 7456MethylparabenHCID 10796Cesium carbonate2 回HCID 126390351-Chloroethan-1-ol

生成物 1

HCID 76670Benzoic acid, 4-(2-hydroxyethoxy)-, methyl ester収率 44%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 4-hydroxybenzoate (1.52 g, 10 mmol), 2-chloroethanol (960 mg, 12 mmol), potassium iodide (100 mg, 0.6 mmol) and cesium carbonate (4.56 g, 14 mmol) are combined with dry THF (50 mL) and the reaction mixture is stirred under reflux for 24 h. Additional chloroethanol (960 mg), cesium carbonate (4.56 g) and potassium iodide (100 mg) are added to the mixture and stirred under reflux for 24 h. The reaction mixture is cooled to room temperature and water and CH2Cl2 are added. The separated CH2Cl2 layer is dried over Na2SO4, filtered and evaporated. The crude product is purified using silica-gel column chromatography (hexane:EtOAc=3:1) to give the titled compound (862 mg, 44%). NMR (CDCl3): δ 8.02 (d, 2H, J=9.0 Hz), 6.97 (d, 2H, J=9.0 Hz), 4.17 (t, 2H, J=5.0 Hz), 4.03 (m, 2H), 3.92 (s, 3H).

後処理

  1. temperatureunder reflux for 24 h
  2. stirringstirred
  3. temperatureunder reflux for 24 h
  4. dry with materialThe separated CH2Cl2 layer is dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified

出典と根拠

ORDレコード
ord-e045882a519d42a8a6f9798cb93f57b3
出典データセット
uspto-grants-2011_05
特許番号
US07951826B2

関連ノート

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