Reaktion #1197428

Reaktionsgleichung

3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

3-phenoxypropyl bromide

sodium iodide

potassium carbonate

→

3-(octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid phenylmethyl ester

Ausbeute 96.0%

Lösungsmittel

acetone

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 46 hours
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Einengenthe filtrate was concentrated to dryness at reduced pressure
4. 4
   workup.ADDITIONWater was added to the residue
5. 5
   Extraktionthe product was extracted with ethyl acetate
6. 6
   ExtraktionThe dried extract
7. 7
   Einengenwas concentrated at reduced pressure to an oil which
8. 8
   Sonstigewas purified by HPLC
9. 9
   Sonstigetriturated with hexane
10. 10
    Filtrationfiltered

Vorschrift

A mixture of 12 g (0.024 mol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 6 ml (0.038 ml) of 3-phenoxypropyl bromide, 3.6 g (0.024 mol) of sodium iodide and 10 g (0.072 mol) of potassium carbonate in 40 ml of acetone and 80 ml of DMF was stirred at reflux for 46 hours. The reaction mixture was filtered and the filtrate was concentrated to dryness at reduced pressure. Water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated at reduced pressure to an oil which was purified by HPLC using 5% ethyl acetate-hexane. The pure fractions were combined, triturated with hexane and filtered to give 14.6 g (96% yield, mp 46°-47°) of 3-(octadecyloxy)-5-(3-phenoxypropoxy)benzoic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

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