반응 #49701

반응 방정식

4-benzyloxybenzoic acid chloride

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

dimethylaminopyridine

triethylamine

→

titled compound

수율 61.2%

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

수율 61.2%

용매

—

ice water

methylene chloride

methylene chloride

반응 조건

후처리

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

실험 절차

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).

출처