Hydrochloric Acid → 1-Nitro-2-phenylethane

HRID 3306

Reaktionsgleichung

Reaktionsgleichung von HRID 3306
[C:1]1([CH:7]=[CH:8][N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].Cl>C(Cl)(Cl)Cl.CC(O)C>[C:1]1([CH2:7][CH2:8][N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 7626Beta-NitrostyreneHCID 4311764Sodium borohydride

Produkt 1

HCID 802081-Nitro-2-phenylethaneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21906603Chloroform isopropyl alcoholLösungsmittel

Versuchsvorschrift

2-Phenylnitroethene (5.12 g, 34.3 mmol, from step 15a) was dissolved in CHCl3 /i-PrOH (410:85 mL) and SiO2 (51.4 g) was added. NaBH4 (5.2 g, 137 mmol) was added in portions, and the mixture was stirred for 90 minutes at room temperature. HCl (0.5N, 100, mL) was added, and the mixture was stirred for 30 minutes. The layers were separated, and the aqueous phase was extracted with methylene chloride. The organic layers were combine, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel (eluting with ether:hexanes 1:30) to give the title compound as an oil (3.89 g, 75%).

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with methylene chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (eluting with ether:hexanes 1:30)

Quellen und Nachweise

ORD-Eintrag
ord-d656571e780d4bccad9fd6471b2c4bc3
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05733912

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