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Hydrochloric Acid → 4,4-Diphenyl-2-formyl-3-(nitromethyl)cyclohexanone

HRID 1196263
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1196263
[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][C:10](=[O:13])[C:9]([CH:14]=[O:15])=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:22]([CH3:25])([O-:24])=[O:23].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.Cl>O1CCCC1.C(O)(C)(C)C.CO.C(OCC)(=O)C.O>[C:1]1([C:7]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][C:10](=[O:13])[CH:9]([CH:14]=[O:15])[CH:8]2[CH2:25][N+:22]([O-:24])=[O:23])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 6375NitromethaneHCID 66854Benzyltrimethylammonium hydroxideHCID 537947534,4-Diphenyl-2-formyl-2-cyclohexen-1-one

Produkt 1

HCID 540830574,4-Diphenyl-2-formyl-3-(nitromethyl)cyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 887
Methanol
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 6386tert-ButanolLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 4,4-diphenyl-2-formyl-2-cyclohexen-1-one (29 g) and nitromethane (5.7 cc) in a mixture of tetrahydrofuran (250 cc) and tert-butanol (500 cc) is treated with a 35% strength solution (6.93 cc) of benzyltrimethylammonium hydroxide in methanol and stirred at 20° C. for 18 hours. The reaction mixture is diluted with ethyl acetate (500 cc) and water (2000 cc) and acidified to pH 2 with hydrochloric acid. The aqueous phase is extracted with ethyl acetate (200 cc) and the combined organic phases are washed with water (500 cc) and saturated sodium chloride solution (250 cc), then dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The crystallized residue is stirred in a mixture (100 cc) of cyclohexane and ethyl acetate (80:20 by volume) and the crystals are drained and washed with the same mixture (20 cc) and with isopropyl ether (2×50 cc). 4,4-Diphenyl-2-formyl-3-(nitromethyl)cyclohexanone (24.7 g) is obtained in the form of cream-colored crystals, m.p. 188° C.

Aufarbeitung

  1. extractionThe aqueous phase is extracted with ethyl acetate (200 cc)
  2. washthe combined organic phases are washed with water (500 cc) and saturated sodium chloride solution (250 cc)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  5. stirringThe crystallized residue is stirred in a mixture (100 cc) of cyclohexane and ethyl acetate (80:20 by volume)
  6. washwashed with the same mixture (20 cc) and with isopropyl ether (2×50 cc)

Quellen und Nachweise

ORD-Eintrag
ord-b44ce0bea8534cb48d4fb4da9a58c4fc
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05112988

Notizen zur Reaktion

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