반응 #1589723

반응 방정식

Methyl 3,4,5-tris(octadecyloxy)cyclohexylcarboxylate

DIBAL

hydrochloric acid

→

3,4,5-tris(octadecyloxy)cyclohexylmethyl alcohol

수율 100.4%

용매

THF

반응 조건

후처리

1. 1
   기타to quench
2. 2
   기타the reaction
3. 3
   기타The solvent was evaporated to about half
4. 4
   workup.DISSOLUTIONthe residue was dissolved in chloroform (700 ml)
5. 5
   세척The mixture was washed three times with 1N hydrochloric acid (300 ml)
6. 6
   기타The solvent was evaporated
7. 7
   기타the residue was precipitated with methanol (700 ml)
8. 8
   세척washed with acetonitrile

실험 절차

Methyl 3,4,5-tris(octadecyloxy)cyclohexylcarboxylate (70.0 g, 73.9 mmol) was dissolved in THF (1050 ml), and DIBAL (1.0 mol/L toluene solution, 200 ml, 200 mmol) was added dropwise at 0° C. over 40 min under a nitrogen atmosphere. After stirring at room temperature for 2 hr, 0.2N hydrochloric acid (50 ml) was added dropwise at 0° C. to quench the reaction. The solvent was evaporated to about half, and the residue was dissolved in chloroform (700 ml). The mixture was washed three times with 1N hydrochloric acid (300 ml), once with 5% aqueous sodium hydrogen carbonate solution (300 ml), and once with 20% brine (300 ml). The solvent was evaporated, and the residue was precipitated with methanol (700 ml), and washed with acetonitrile to give 3,4,5-tris(octadecyloxy)cyclohexylmethyl alcohol (68.2 g, 74.2 mmol, 100%).

출처