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

HRID 552574

Reaktionsgleichung

Reaktionsgleichung von HRID 552574
[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

Komponenten

9

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e045882a519d42a8a6f9798cb93f57b3
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951826B2

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