4-Hydroxybenzoic Acid → HCID 22242581, compound

HRID 1070377Notes

Reaction equation

HRID 1070377 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.OC1C=CC(C(O)=O)=CC=1.[Na+].[I-:26].[OH-].[Na+].[O-]Cl.[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].Cl>CO>[I:26][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:12]([OH:14])=[O:13])=[CH:8]2

Participants

9

Reactant 7

HCID 1354-Hydroxybenzoic AcidHCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 855576-Hydroxy-2-naphthoic acidHCID 656671Sodium PyrosulfiteHCID 23665760Sodium Hypochlorite

Product 1

HCID 22242581HCID 22242581, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

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

Workup

  1. temperatureThe solution was cooled to 0□C
  2. extractionextracted with 40 ml of ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationThe solution was concentrated to an off-white solid, that
  6. customwas recrystallized from toluene/CH3OH

Sources & evidence

ORD record
ord-11f3deb8fd7d47e88000ec4028e8075d
Source dataset
uspto-grants-2005_06
Patent number
US06902908B2

Reaction notes

Loading…