반응 #2267060

반응 방정식

6-hydroxy-2-naphthoic acid

NaOCl

sodium metabisulfite

HCl

4-hydroxybenzoic acid

NaI

NaOH

→

5-iodo-6-hydroxy-2-naphthoic acid

용매

MeOH

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise over 75 min
2. 2
   추출extracted with 40 ml of ether
3. 3
   세척The organic layer was washed with brine
4. 4
   건조dried over MgSO4
5. 5
   농축The solution was concentrated to an off-white solid, that
6. 6
   기타was recrystallized from toluene/CH3OH

실험 절차

Mono-iodination of 6-hydroxy-2-naphthoic acid and 4-hydroxybenzoic acid was carried out following the procedure of Edgar and Falling (J. Org. Chem. 55, 5287, 1990). Thus, 0.75 gm of (4.34 mmol) was dissolved in 19 ml of MeOH and 1.04 gm of NaI (and 0.27 gm of NaOH was added. The solution was cooled to O▪C and aqueous NaOCl (4% solution, 12.9 ml) was added dropwise over 75 min. The resulting mixture was stirred for 1 hr at 0° C. and then treated with 7 ml of 10% aqueous sodium metabisulfite. The mixture was adjusted to pH 7 using 5% HCl and extracted with 40 ml of ether. The organic layer was washed with brine and dried over MgSO4. The solution was concentrated to an off-white solid, that was recrystallized from toluene/CH3OH to provide 0.42 gm of 5-iodo-6-hydroxy-2-naphthoic acid. Reaction of 6′-Tostylatractviloside with 1.2-ethylenediamine

출처