Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 2-(2-Chloroethoxy)benzaldehyde

HRID 867907

Reaktionsgleichung

Reaktionsgleichung von HRID 867907
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:10][CH2:11][CH2:12]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:10][CH2:11][CH2:12][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 6998SalicylaldehydeHCID 11430Potassium Carbonate

Produkt 1

HCID 38414102-(2-Chloroethoxy)benzaldehydeAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

40.0 g of 2- hydroxybenzaldehyde, 84 g of 1-chloro-2-tosyloxyethane and 50 g of potassium carbonate are added to 270 ml of dimethylformamide, and the mixture is stirred at room temperature for 3 days. After the reaction, half of the solvent is distilled off under reduced pressure. About 600 ml of water are added to the residue, and the mixture is extracted with ether. The extract is washed with 10% sodium hydroxide solution and water, dried and then distilled to remove the solvent. The residue is distilled at 116°-118° C./0.2-0.3 mmHg to give 2-(2-chloroethyloxy)benzaldehyde (51.9 g, yield: 86%) as a coloress oil. The properties of this compound are the same as those disclosed in J.O.C., 18, 1380-1402 (1953).

Aufarbeitung

  1. customAfter the reaction, half of the solvent
  2. distillationis distilled off under reduced pressure
  3. additionAbout 600 ml of water are added to the residue
  4. extractionthe mixture is extracted with ether
  5. washThe extract is washed with 10% sodium hydroxide solution and water
  6. customdried
  7. distillationdistilled
  8. customto remove the solvent
  9. distillationThe residue is distilled at 116°-118° C./0.2-0.3 mmHg

Quellen und Nachweise

ORD-Eintrag
ord-3477590f4ad34286b63e28571ef0e6ef
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04777178

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