Benzaldehyde → 2-Nitro-1-phenylbutan-1-ol

HRID 2107369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2107369
[N+:1]([CH2:4][CH2:5][CH3:6])([O-:3])=[O:2].C(N(CC)CC)C.[Cl-].[Cl-].C([Al+2])C.[CH:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:20]1([CH:19]([OH:26])[CH:4]([N+:1]([O-:3])=[O:2])[CH2:5][CH3:6])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 79031-NitropropaneHCID 8471TriethylamineHCID 16686341Ethyl aluminium dichloride

Produkt 1

HCID 2261232-Nitro-1-phenylbutan-1-olAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of nitropropane (0.45 g, 0.005 moles) in dichloromethane (25 mL) at 0° C. was added triethylamine (0.67 mL, 0.005 moles) followed by ethyl aluminum dichloride (1.0 M in hexane, 5 mL, 0.005 moles). After 15 minutes benzaldehyde (0.5 mL 0.005 moles) was added and the solution allowed to warm to room temperature. After a further 3 hours the reaction was cooled in ice to a temperature of 5° C. and quenched with pH 7.0 phosphate buffer. The organic layer was separated, dried and evaporated in vacuo. Flash column chromatography [SiO2, 6:1 hexane, Et2O] gave 1-phenyl-2-nitro-1-butanol (0.28 g, 29%) Erythro:threo ratio 1:1.6.

Aufarbeitung

  1. temperatureAfter a further 3 hours the reaction was cooled in ice to a temperature of 5° C.
  2. customquenched with pH 7.0 phosphate buffer
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d8a18e7ed19a42ab9a50f5bb802ded73
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04933505

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