Bromobenzene → 2-Chloro-1,1-diphenylethanol

HRID 1906714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1906714
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].[CH2:9]([Cl:18])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[Cl-].[NH4+]>[Na].C(OCC)C>[C:2]1([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([OH:11])[CH2:9][Cl:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 7961BromobenzeneHCID 107572-ChloroacetophenoneHCID 25517Ammonium ChlorideHCID 5462224Magnesium2×

Produkt 1

HCID 2325962-Chloro-1,1-diphenylethanolAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 5360545SodiumLösungsmittel

Versuchsvorschrift

Bromobenzene (0.2 mol, 31.4 g) in sodium dry diethyl ether (200 ml) was added dropwise to magnesium (0.22 gram atoms, 5.3 g). After all the magnesium had reacted, phenacyl chloride (0.1 mol, 15.5 g) in diethyl ether (100 ml) was added dropwise and the solution stirred at room temperature for 1 hour. The reaction mixture was poured into saturated ammonium chloride solution, washed with water (3×150 ml), and dried (Na2SO4). Removal of the ether gave a pale yellow oil which solidified on standing. Recrystallisation from petroleum ether (60°-80°) gave 1,1-diphenyl-2-chloro-ethan-1-ol (60%) as a white crystalline solid, m.p. 56°-57°.

Aufarbeitung

  1. washwashed with water (3×150 ml)
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the ether
  4. customgave a pale yellow oil which
  5. customRecrystallisation from petroleum ether (60°-80°)

Quellen und Nachweise

ORD-Eintrag
ord-30f9e63d5de24dc89f24f33a0d075af0
Quelldatensatz
uspto-grants-1987_03
Patentnummer
US04654332

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