Sodium hydride → 4-(4-Phenylbutoxy)-1,2-dinitrobenzene

HRID 412696

Reaktionsgleichung

Reaktionsgleichung von HRID 412696
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[N+:14]([C:17]1[CH:18]=[C:19](Cl)[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])([O-:16])=[O:15]>C1COCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:19]2[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:17]([N+:14]([O-:16])=[O:15])[CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 330974-Chloro-1,2-dinitrobenzeneHCID 76889Benzenebutanol

Produkt 1

HCID 185379134-(4-Phenylbutoxy)-1,2-dinitrobenzeneAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Phenyl-1-butanol (1 mL, 6.49 mmol) in THF (3 mL) was combined under dry nitrogen with sodium hydride (0.26 g, 6.5 mmol) in a 60% mineral oil dispersion. The mixture was stirred vigorously for 5 minutes, combined with 3,4-dinitrochlorobenzene (1.3 g, 6.42 mmol) and then stirred 10 hours at room temperature. The mixture was partitioned between diethyl ether and 3N hydrochloric acid. The aqeuous layer was separated and extracted several times with diethyl ether. The combined organic layers were dried (MgSO4), filtered and concentrated by rotary evaporation. The residue was purfied by flash chromatography (9:1 hexanes/diethyl ether) to provide 4-(4-phenylbutoxy)-1,2-dinitrobenzene (1.16 g, 72% yield); 1H-NMR (300 Mhz, CDCL3): 7.84 (d, 1H, J=10.0 Hz), 7.19-7.36 (m, 5H), 7.00-7.06 (m, 2H), 4.10 (t, 2H, J=5.7 Hz), 2.73 (t, 2H, J=6.5 Hz), 1.89 (m, 4H).

Aufarbeitung

  1. stirringstirred 10 hours at room temperature
  2. customThe mixture was partitioned between diethyl ether and 3N hydrochloric acid
  3. customThe aqeuous layer was separated
  4. extractionextracted several times with diethyl ether
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-18edf7757a4747c7a02c3776e4fa8613
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562854B2

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