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Nitrogen → 1,6-Bis[4-(3-hydroxypropyl)phenoxy]hexane

HRID 51286
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 51286
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.I[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]I.N#N.[C:22](=[O:25])([O-])[O-].[K+].[K+]>CS(C)=O>[OH:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:22][OH:25])=[CH:4][CH:3]=2)=[CH:7][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 123731,6-DiiodohexaneHCID 824523-(4-Hydroxyphenyl)propanol

Produkt 1

HCID 219598591,6-Bis[4-(3-hydroxypropyl)phenoxy]hexaneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 3-(4-hydroxyphenyl)-1-propanol 35 (3.3 g, 21.7 mmole) and 1,6-di-iodohexane (3.5 g, 8.88 mmole) in dimethylsulfoxide (40 mL) was degassed and saturated with N2 gas and potassium carbonate (4.5 g, 32.56 mmole) was added. The reaction mixture was stirred at 80° C. for 18 h under nitrogen atmosphere and then quenched with brine (150 mL). The product was extracted with EtOAc (200 mL) and the organic extracts were washed with 0.1 M NaOH and brine, and dried with MgSO4. The organics were removed in vacuo to give a pale brown solid. The solid was purified by flash silica column chromatography: 4/1 hexane/EtOAc to 5% MeOH in 1/1 hexane/EtOAc to give 1,6-bis[4-(3-hydroxypropyl)phenoxy]hexane 36 (Rf=0.17 in 1/1 hexane/EtOAc) in 65% yield (2.23 g). 1H-NMR (CD3OD, 299.96 MHz): δ (ppm) 7.08-7.05 (d, 4H), 6.80-6.77 (d, 4H), 3.93-3.89 (t, 4H), 3.56-3.52 (t, 4H), 2.64-2.56 (t, 4H), 1.81-1.69 (m, 8H), 1.44-1.21 (m, 4H).

Aufarbeitung

  1. additionwas added
  2. customquenched with brine (150 mL)
  3. extractionThe product was extracted with EtOAc (200 mL)
  4. washthe organic extracts were washed with 0.1 M NaOH and brine
  5. dry with materialdried with MgSO4
  6. customThe organics were removed in vacuo
  7. customto give a pale brown solid
  8. customThe solid was purified by flash silica column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b4e770601f45454db6e4faf14ec4e779
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06713651B1

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