반응 #526851

반응 방정식

Jones reagent

water

3,4,4-trifluoro-3-buten-1-ol

Jones reagent

water

→

3,4,4-trifluoro-3-butenoic acid

수율 65.0%

desired product

수율 65.0%

용매

acetone

acetone

반응 조건

후처리

1. 1
   온도A reaction temperature of 51°-54° C. was maintained
2. 2
   workup.ADDITIONthe addition (45 min)
3. 3
   온도to cool to 35°-40° C. over 30-60 min
4. 4
   기타The reaction mixture was transferred to a separatory funnel
5. 5
   기타layers separated
6. 6
   세척The upper layer was washed once with brine
7. 7
   농축concentrated
8. 8
   workup.ADDITIONThe lower layer was diluted with water (500 mL)
9. 9
   추출extracted with dichloromethane (3 L)
10. 10
    추출The dichloromethane extract
11. 11
    세척washed with brine
12. 12
    건조dried over magnesium sulfate
13. 13
    기타Evaporation of the solvent

실험 절차

A mechanically stirred 12 L glass reactor clad with a jacket cooled with tap water was charged with 100 mL of acetone and 100 mL of Jones reagent. A solution of 3,4,4-trifluoro-3-buten-1-ol (850 g, 6.75 mol) diluted to a total volume of 5.0 L in acetone was added simultaneously with 5.0 L of Jones reagent via a twin head peristaltic pump capable of of a pump rate ca. 120 mL/min. A reaction temperature of 51°-54° C. was maintained by adjusting the pump rate and the tap water cooling flow. Following the addition (45 min), the mixture was allowed to cool to 35°-40° C. over 30-60 min. The reaction mixture was transferred to a separatory funnel and layers separated. The upper layer was washed once with brine and concentrated. The lower layer was diluted with water (500 mL) and extracted with dichloromethane (3 L). The dichloromethane extract was combined with the above residue, washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave 613 g (65%) of the desired product as a green oil.

출처