2-Chlorobenzyl chloride → 1-Chloro-2-(4-chlorophenyl)-3-(2-chlorophenyl)propan-2-ol

HRID 326439

Reaktionsgleichung

Reaktionsgleichung von HRID 326439
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[Mg].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:21])[CH2:19][Cl:20])=[CH:14][CH:13]=1.[Cl-].[NH4+]>CCOCC.C1(C)C=CC=CC=1>[Cl:20][CH2:19][C:18]([C:15]1[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=1)([OH:21])[CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1]

Komponenten

7

Edukt 4

HCID 119062-Chlorobenzyl chloride2×HCID 25517Ammonium ChlorideHCID 702982,4'-DichloroacetophenoneHCID 5462224Magnesium

Produkt 1

HCID 150551621-Chloro-2-(4-chlorophenyl)-3-(2-chlorophenyl)propan-2-olAusbeute 949,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5.0 g (0.031 mol) of 2-chlorobenzyl chloride are added within 5 minutes at from 24° to 36° C. to 9.7 g (0.404 mol) of magnesium turnings in 20 ml of absolute ether. After the reaction has commenced, a solution of 200 ml of absolute ether and 50.2 g (0.31 mol) of 2-chlorobenzyl chloride is added dropwise. The mixture is subsequently refluxed for about a further 10 minutes, the excess magnesium is decanted off under nitrogen, and the Grignard solution is cooled to 0° C. 55.7 g (0.3 mol) of para-chloro-ω-chloroacetophenone dissolved in 350 ml of toluene are then added dropwise, and the reaction mixture is stirred at 0° C. for 1.5 hours and added dropwise at from about 2° to 6° C. to 1.5 l of concentrated ammonium chloride solution. Extraction with methyl tert.-butyl ether and subsequent conventional work-up gives 92.9 g (yield 99%, purity according to HPLC: 68.2%) of 1-chloro-2-(4-chlorophenyl)-3-(2-chlorophenyl)propan-2-ol as a crude oil, which can be further reacted directly. For characterization, the product was recrystallized from n-hexane.

Aufarbeitung

  1. temperatureThe mixture is subsequently refluxed for about a further 10 minutes
  2. customthe excess magnesium is decanted off under nitrogen
  3. additionare then added dropwise
  4. extractionExtraction with methyl tert.-butyl ether and subsequent conventional work-up

Quellen und Nachweise

ORD-Eintrag
ord-d02e5b4173d74de9a73a53cb78b9e5d1
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05268517

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