Acetic Acid → 1-Benzyloxy-4-(2-nitro-ethyl)-benzene

HRID 78279

Reaktionsgleichung

Reaktionsgleichung von HRID 78279
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.CS(C)=O.[B-].[Na+]>O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N+:17]([O-:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 5702926(E)-1-(Benzyloxy)-4-(2-nitrovinyl)benzeneHCID 22959485Vertellus

Produkt 1

HCID 247210371-Benzyloxy-4-(2-nitro-ethyl)-benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

While cooling using a water bath, to a mixture of 1-benzyloxy-4-((E)-2-nitro-vinyl)-benzene described in Manufacturing Example 229-1-1 (60 g, 0.23 mol), acetic acid (27 mL) and dimethyl sulfoxide (400 mL) was added sodium borohydrate (8.9 g, 0.23 mol), which was stirred for 20 minutes at room temperature. Water (2.5 L) was added dropwise to the reaction mixture, and the deposited solids were filtered. Diethyl ether (300 mL) was added to the obtained solids to dissolve the title compound, and separation into filtrate and solids was carried out by filtration. The filtrate was concentrated under a reduced pressure to obtain the title compound (39 g). On the other hand, diethyl ether (300 mL) was added to the previously separated solid to dissolve the title compound, and separation into filtrate and solids was carried out by filtration. The filtrate was concentrated under a reduced pressure to obtain the title compound (12 g). This was combined with the previously obtained solids to obtain the title compound (51 g) as a crude product.

Aufarbeitung

  1. temperatureWhile cooling
  2. filtrationthe deposited solids were filtered
  3. additionDiethyl ether (300 mL) was added to the obtained solids
  4. dissolutionto dissolve
  5. customthe title compound, and separation into filtrate and solids
  6. filtrationwas carried out by filtration
  7. concentrationThe filtrate was concentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a3349ff6394d4fd3981d78e8162ad706
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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