Hydrochloric Acid → 3-((3-Methoxyphenyl)methyl)cyclohexanone

HRID 377309Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 377309
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][Mg]Cl.[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13]1.C[Si](Cl)(C)C.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH:14]1[CH2:15][CH2:16][CH2:17][C:12](=[O:18])[CH2:13]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 135942-Cyclohexen-1-oneHCID 178490222HCID 178490222, Verbindung

Produkt 1

HCID 193584913-((3-Methoxyphenyl)methyl)cyclohexanoneAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-methoxybenzylmagnesium chloride (19.8 mole) in tetrahydrofuran (20 ml) was added a mixture of 2-cyclohexen-1-one (1.9 g) and trimethylsilyl chloride (5.8 ml) in tetrahydrofuran (30 ml) at -78° C. under N2. The mixture was stirred for 1 hour at 0° C. The reaction mixture was poured into a mixture of ethyl acetate and 1N-hydrochloric acid and the organic layer was washed with saturated sodium bicarbonate aqueous solution and brine. The combined organic extracts were concentrated and the residue was purified by column chromatography on silica gel to give 3-(3-methoxybenzyl)cyclohexanone (2.12 g).

Aufarbeitung

  1. washthe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  2. concentrationThe combined organic extracts were concentrated
  3. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f7d8ff0ef89e4174b799a4d5af5f0e00
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025375

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