Reaktion #79564

Reaktionsgleichung

3-(4-hydroxyphenyl)-1-propanol

1,6-di-iodohexane

N2

potassium carbonate

→

1,6-bis[4-(3-hydroxypropyl)phenoxy]hexane

Ausbeute 65.0%

Lösungsmittel

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Sonstigequenched with brine (150 mL)
3. 3
   ExtraktionThe product was extracted with EtOAc (200 mL)
4. 4
   Waschenthe organic extracts were washed with 0.1 M NaOH and brine
5. 5
   Trocknendried with MgSO4
6. 6
   SonstigeThe organics were removed in vacuo
7. 7
   Sonstigeto give a pale brown solid
8. 8
   SonstigeThe solid was purified by flash silica column chromatography

Vorschrift

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).

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