Acetic Anhydride → acetic acid (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexyl ester

HRID 73493Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 73493
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:16]([N+:17]([O-:19])=[O:18])[CH2:15][CH2:14][CH:13]([OH:20])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:21](OC(=O)C)(=[O:23])[CH3:22]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:16]([N+:17]([O-:19])=[O:18])[CH2:15][CH2:14][CH:13]([O:20][C:21](=[O:23])[CH3:22])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Komponenten

3

Edukt 2

HCID 7918Acetic AnhydrideHCID 17989075(1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanol2×

Produkt 1

HCID 67022378acetic acid (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexyl ester

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

10.18 g of (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocydohexanol (compound D2) are dissolved in 100 ml of acetic anhydride and the solution is heated to 100° C. for 1-2 h. After removal of the solvent, the residue is chromatographed on silica gel using a mixture of petroleum ether/ethyl acetate in the ratio 2/1. Concentration of the corresponding eluate fractions furnish 10.37 g (89% of theory) of the title compound as an oil.

Aufarbeitung

  1. customAfter removal of the solvent
  2. customthe residue is chromatographed on silica gel using
  3. additiona mixture of petroleum ether/ethyl acetate in the ratio 2/1

Quellen und Nachweise

ORD-Eintrag
ord-92579535052540ec95de14424f4d8df3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829189B2

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