4-Hydroxybenzoic Acid → HCID 22242581, compound

HRID 1071820Notes

Reaction equation

HRID 1071820 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 nd 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-iodo6-hydroxy-2-naphthoic acid. Reaction of 6′-Tostylatractyloside with 1.2-ethylenediamine

Workup

  1. additionwas added dropwise over 75 min
  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-b6b06188fb814a05a4b03ea319420549
Source dataset
uspto-grants-2005_06
Patent number
US06906174B2

Reaction notes

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