Water → 2-Hydroxy-2-phenylcyclopentanone

HRID 1704214

Reaktionsgleichung

Reaktionsgleichung von HRID 1704214
[C:1]1(=[O:7])[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[C:8]1([Li])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>CCOCC>[OH:6][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:3][CH2:4][CH2:5][C:1]1=[O:7]

Komponenten

5

Edukt 3

HCID 962WaterHCID 5666571,2-CyclopentanedioneHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 105834112-Hydroxy-2-phenylcyclopentanoneAusbeute 58,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

A solution of 73.5 g (0.75 mole) of 1,2-cyclopentanedione in 400 ml of ether was added to 1.5 moles of phenyl lithium in 1.2 liter of ether, and the mixture was stirred under N2 for one half hour. After careful addition of water, the ethereal layer was separated, dried over magnesium sulfate and the solvent evaporated. The residue was distilled under reduced pressure and gave 77.2 g of 2-hydroxy-2-phenylcyclopentanone, b.p. 122°-126° C. (1.5 mm), nD25 1.5551. The oxime was prepared by known procedures, m.p. 110°-112° C., and was reduced by hydrogenation over Raney nickel in 20% alcoholic ammonia. Removal of catalyst, evaporation of solvent and addition of HCl gave 2-hydroxy-2-phenylcyclopentylamine hydrochloride, m.p. 198°-199° C.

Aufarbeitung

  1. customthe ethereal layer was separated
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent evaporated
  4. distillationThe residue was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6259cad6f41344e088ca537381a58f0d
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04126611

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