Water → 2-Chloro-6-phenoxybenzenemethanol

HRID 1956593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1956593
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[CH:4]=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[CH2:4][OH:5]

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 186636022-Chloro-6-phenoxybenzaldehydeHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 223783762-Chloro-6-phenoxybenzenemethanolAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

19.0 g (77.67 mmol) of 2-chloro-6-phenoxy-benzaldehyde in approximately 40 ml of tetrahydrofuran are added dropwise at room temperature in the course of 30 minutes to a suspension of 4.42 g (116.5 mmol) of lithium aluminium hydride in approximately 150 ml of tetrahydrofuran. The mixture is then heated under reflux for 4 hours, cooled and hydrolysed with 4.4 ml of water, 4.4 ml of 4N sodium hydroxide and 13.2 ml of water. The reaction mixture is boiled under reflux for 30 minutes, cooled and filtered, and the suction filter residue is 3× taken up in ethyl acetate, boiled under reflux for 15 minutes and filtered. The combined filtrates are concentrated. 17.97 g (76.57 mmol)=94% of crude (2-chloro-6-phenoxy-phenyl)-methanol are obtained in the form of a yellow oil; TLC (silica gel; ethyl acetate/hexane=1:1; UV): Rf =0.68; 1H-NMR (CDCl3, 200 MHz): 4.90 (s, 2H); 6.76-7.40 (m, 8H).

Aufarbeitung

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 4 hours
  3. temperatureunder reflux for 30 minutes
  4. temperaturecooled
  5. filtrationfiltered
  6. filtrationthe suction filter residue
  7. temperatureunder reflux for 15 minutes
  8. filtrationfiltered
  9. concentrationThe combined filtrates are concentrated

Quellen und Nachweise

ORD-Eintrag
ord-090b2c4b263b4e7285e3c7e5b836cb3d
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780501

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