Salicyl Alcohol → [2-(2-Chlorobenzyloxy)phenyl]methanol

HRID 1672667

Reaktionsgleichung

Reaktionsgleichung von HRID 1672667
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]

Komponenten

5

Edukt 3

HCID 5146Salicyl AlcoholHCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotoluene

Produkt 1

HCID 961592[2-(2-Chlorobenzyloxy)phenyl]methanolAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 2.42 g (19.47 mmol) of 2-hydroxybenzyl alcohol in 100 ml of dry acetonitrile is mixed with 4.12 g (19.47 mmol) of 2-chlorobenzyl bromide and 2.96 g (21.42 mmol) of anhydrous potassium carbonate and heated to reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution and dried over sodium sulfate. The organic phase is concentrated. The resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3). 3.856 g (15.5 mmol, 79% yield) of a solid are obtained.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationThe organic phase is concentrated
  7. customThe resulting crude product is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-8e3f0e4268514c848443ca63c3a9b4c0
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998988B2

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