4-Hydroxybenzoic Acid → HCID 22242581, compound

Participants

Reaction Conditions

Reaction Steps

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 0□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′-Tostylatractyloside with 1,2-ethylenediamine

Provenance & Evidence