Reaktion #49701

Reaktionsgleichung

4-benzyloxybenzoic acid chloride

(R)-(+)-1,1,1-trifluoro-2-octanol

dimethylaminopyridine

triethylamine

→

titled compound

Ausbeute 61.2%

1,1,1-trifluoro-2-octyl 4-benzyloxybenzoate

Ausbeute 61.2%

Lösungsmittel

—

ice water

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe mixture was left
2. 2
   SonstigeThe methylene chloride layer separated
3. 3
   Waschenwas washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order
4. 4
   Trocknendried over magnesium sulfate
5. 5
   workup.DISTILLATIONdistilled
6. 6
   Sonstigeto obtain a crude objective compound
7. 7
   SonstigeThe compound was purified by toluene/silica gel chromatography and recrystallization from ethanol

Vorschrift

To a solution of 4-benzyloxybenzoic acid chloride (4.3 g) in methylene chloride (50 ml) was added drop by drop a solution of (R)-(+)-1,1,1-trifluoro-2-octanol (2.9 g), dimethylaminopyridine (0.6 g) and triethylamine (1.7 g) in methylene chloride (50 ml), under ice cooling. The mixture was left to stand at the room temperature for 24 hours before being poured in ice water. The methylene chloride layer separated was washed with diluted hydrochloric acid, water 1N aqueous sodium carbonate solution and water in this order, dried over magnesium sulfate and distilled to obtain a crude objective compound. The compound was purified by toluene/silica gel chromatography and recrystallization from ethanol to obtain the titled compound (3.8 g).

Quelle