Methyl Acrylate → Rac-4-cyclohexyl-4-nitro-butyric acid methyl ester

HRID 2177486Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2177486
[N+:1]([CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)([O-:3])=[O:2].[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13]>C(O)(C)(C)C.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.CO.O>[CH3:16][O:15][C:11](=[O:14])[CH2:12][CH2:13][CH:4]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[N+:1]([O-:3])=[O:2]

Komponenten

7

Edukt 2

HCID 7294Methyl AcrylateHCID 220634(Nitromethyl)cyclohexane

Produkt 1

HCID 59438496Rac-4-cyclohexyl-4-nitro-butyric acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 66854Benzyltrimethylammonium hydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 3.18 g (22.2 mmol) nitromethyl-cyclohexane (CAS: 2625-30-1) in 1 ml tert-butanol and 0.12 ml 35% benzyltrimethylammonium hydroxide in methanol warmed to 40° C. were added 1.99 ml (22.2 mmol) methyl acrylate. The yellow mixture was stirred at 40° C. for 2 hours then diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, filtered and evaporated. The title compound was obtained in as slightly yellow oil: MS (EI): 198 (M.+−MeO), 183 (M.+−NO2), 151 (M−(MeO+NO2+H)).+ (100%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-96e1426b49f64e8294b979625162717f
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067911B2

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