4-Hydroxybenzoic Acid → HCID 22242581, compound

HRID 890911Notes

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

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.

Workup

additionwas added dropwise over 75 min
extractionextracted with 40 ml of ether
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationThe solution was concentrated to an off-white solid, that
customwas recrystallized from toluene/CH3OH

Sources & evidence

ORD record: ord-1779dc59bfb44e36836bee62be71d83a
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001729B2

Reaction notes

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