Reaktion #1197432

Reaktionsgleichung

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

methyl 5-bromovalerate

potassium carbonate

sodium iodide

→

3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]benzoic acid phenylmethyl ester

Ausbeute 92.5%

Lösungsmittel

acetone

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux under argon for 40 hours
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   Einengenthe filtrate was concentrated at reduced pressure to a solid which
4. 4
   Sonstigewas recrystallized from methylene chloride-methanol

Vorschrift

A mixture of 10.0 g (0.02 mol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 4.3 ml (0.03 mol) of methyl 5-bromovalerate, 5.6 (0.04 mol) of potassium carbonate and 3.0 g (0.02 mol) of sodium iodide in 300 ml of acetone and 75 ml of DMF was stirred at reflux under argon for 40 hours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure to a solid which was recrystallized from methylene chloride-methanol to give 11.3 g (92% yield, mp 40°-42°) of 3-(octadecyloxy)-5-[(5-methoxy-5-oxopentyl)oxy]benzoic acid phenylmethyl ester. The structure was confirmed by nmr and mass spectra.

Quelle