Reaktion #216537

Reaktionsgleichung

2,4,6-triiodophenol

2-ethylhexanoyl chloride

hydrochloric acid

→

oil

Ausbeute 119.4%

2,4,6-Triiodophenyl 2-ethylhexanoate

Ausbeute 119.4%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous solution was extracted twice with ethyl acetate
2. 2
   WaschenThe combined organic layers were washed with aqueous hydrochloric acid, water, saturated aqueous sodium chloride
3. 3
   Trocknendried over magnesium sulfate
4. 4
   EinengenThe ethyl acetate solution was then concentrated under vacuum

Vorschrift

A solution of 2,4,6-triiodophenol (20.0 g, 42 mmol), 2-ethylhexanoyl chloride (25 ml, 144 mmol, 3.5 eq.) and 4-dimethylaminopyridine (DMAP; 2 mmol, 250 mg, 0.05 eq.) in 150 ml of pyridine was stirred overnite at room temperature. The solution was poured into 1000 ml of 1N aqueous hydrochloric acid and the aqueous solution was extracted twice with ethyl acetate. The combined organic layers were washed with aqueous hydrochloric acid, water, saturated aqueous sodium chloride and then dried over magnesium sulfate. The ethyl acetate solution was then concentrated under vacuum to give an oil (30 g) which was purified by silica gel chromatography (5% ethyl acetate/hexanes eluent) to give the product. Concentration under high vacuum afforded 21 g (79%) of the desired hexanoate ester as an oil. The product was taken up in hexanes and filtered through a pad of basic alumina. The filtrate was concentrated under high vacuum to give 16.9 g of analytically pure product.

Quelle