Ethanol → Ethyl 4-chloro-3-hydroxybenzoate

HRID 2064777Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064777
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].S(=O)(=O)(O)O.O.C([O-])(O)=O.[Na+].[CH3:23][CH2:24]O>CCOCC>[CH2:23]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([OH:11])[CH:4]=1)[CH3:24]

Komponenten

7

Edukt 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 1418724-Chloro-3-hydroxybenzoic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 58847555Ethyl 4-chloro-3-hydroxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-3-hydroxy-benzoic acid (29.3 mmol) in EtOH (110 mL) is treated with conc. sulfuric acid (23.6 mL) and heated to reflux for 16 h. Water (600 mL), NaHCO3 (100 g) and ether (300 mL) are added successively, the layers are separated and the aqueous layer is extracted twice with ether. The combined organic layers are washed twice with brine, dried over MgSO4 and concentrated in vacuo to give the desired product which is used without further purification. 1H-NMR (CDCl3): δ=7.73 (s, 1H); 7.58 (d, J=8.3 Hz, 1H); 7.40 (d, J=8.3 Hz, 1H); 5.87 (s, 1H); 4.39 (q, J=7.0 Hz, 2H); 1.41 (t, J=7.0 Hz, 3H).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. customthe layers are separated
  4. extractionthe aqueous layer is extracted twice with ether
  5. washThe combined organic layers are washed twice with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-58421913474c4111beaf72de0d6e9975
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288435B2

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