반응 #87459

반응 방정식

1

2,3-dihydroxyterephthalic acid

benzyl chloride

K2CO3

→

oil

수율 48.0%

Dibenzyl 2,3-bis(benzyloxy)terephthalate

수율 48.0%

용매

DMF

반응 조건

후처리

1. 1
   기타yielding
2. 2
   workup.ADDITIONa mixture of dark brown solution
3. 3
   기타The flask was fitted with a reflux condenser and mechanical stirrer
4. 4
   여과filtered
5. 5
   workup.DISSOLUTIONbrown, viscous oil, which was dissolved in ˜600 mL DCM
6. 6
   여과The opaque, brown solution was filtered
7. 7
   추출extracted with water (5×500 mL)
8. 8
   건조The organic layer was dried with MgSO4
9. 9
   기타This oil was purified by silica column chromatography (0-5% MeOH in DCM)

실험 절차

1 (101.798 g, 0.514 mol), benzyl chloride (258 mL, 2.242 mol), KI (25.304 g, 0.140 mol), K2CO3 (664.270 g, 4.806 mol), and 1.3 L DMF were combined in a 5-L 3-neck round-bottom flask, yielding a mixture of dark brown solution and undissolved solid. The flask was fitted with a reflux condenser and mechanical stirrer, and placed in a heating mantle. The reaction mixture was heated at 67° C. for 3 d and filtered. The dark brown, clear filtrate was rotovapped to ˜400 mL of opaque, brown, viscous oil, which was dissolved in ˜600 mL DCM. The opaque, brown solution was filtered and extracted with water (5×500 mL). A small amount of brine was used to break up emulsions. The organic layer was dried with MgSO4 and rotovapped to ˜250 mL of dark brown oil. This oil was purified by silica column chromatography (0-5% MeOH in DCM) to yield a hardened brown oil (48%).

출처