Butyl bromide → 5-(1-Butyloxy)-2-nitrobenzyl alcohol

HRID 862664

Reaktionsgleichung

Reaktionsgleichung von HRID 862664
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7][OH:8].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH3:22]>CN(C)C(=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7][OH:8])[CH2:20][CH2:21][CH3:22]

Komponenten

5

Edukt 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 1089463-(Hydroxymethyl)-4-nitrophenol

Produkt 1

HCID 540218025-(1-Butyloxy)-2-nitrobenzyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

5.1 g (30 mmol) of 5-hydroxy-2-nitrobenzyl alcohol were stirred with 2.5 g (18 mmol) of potassium carbonate and 25 ml of N,N-dimethylacetamide at 70°-80° C. for 30 minutes. After cooling to 20° C., 3.9 ml (36 mmol) of 1-butylbromide were added dropwise and the mixture was stirred at 90° C. for 2 hours. After cooling, the reaction mixture was concentrated in vacuo, the residue was treated with water and the pH was brought to 7 with 2N HCl. The oil obtained crystallizes after about 30 minutes; the product was filtered off with suction, washed with water and dried; 6 g, melting point 47°-49° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionthe residue was treated with water
  4. customThe oil obtained
  5. customcrystallizes after about 30 minutes
  6. filtrationthe product was filtered off with suction
  7. washwashed with water
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-eab0bfe592004e65b31fefd351a48f31
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05719164

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