Phloroglucinol → 11-Nitroundecanoic Acid tert-butyl Ester

HRID 44120

Reaktionsgleichung

Reaktionsgleichung von HRID 44120
[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br)([CH3:4])([CH3:3])[CH3:2].[N:19]([O-:21])=[O:20].[Na+].C1(C=C(O)C=C(O)C=1)O>CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N+:19]([O-:21])=[O:20])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 359PhloroglucinolHCID 11088520Tert-butyl 11-bromoundecanoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 8608841911-Nitroundecanoic Acid tert-butyl EsterAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

In a 100 ml two-neck round bottom flask 11-bromoundecanoic acid t-butyl ester (6.10 g, 19.0 mmol) was dropped into a stirred solution of NaNO2 (2.60 g, 38.0 mmol) and phloroglucinol (3.10 g, 19.0 mmol) in DMF (10 ml). The reaction mixture was warmed at 50° C. and stirred for 24 h, then poured into a mixture of 40 mL of ice/water and 40 mL of PET. After separation, the aqueous phase was further extracted with PET (3×30 mL), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by silica-gel column chromatography (PET/diethyl ether 95/5) obtaining a light yellow solid (2.29 g, 42%). M.p. 39-42° C. ESI-MS: 288 (MH+); (Calc. for C15H29NO4: 287 u.m.a.).

Aufarbeitung

  1. customAfter separation
  2. extractionthe aqueous phase was further extracted with PET (3×30 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica-gel column chromatography (PET/diethyl ether 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-550b1a50d4de424d8c7cea758a8c3b5e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08540966B2

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