Hydrochloric Acid → HCID 25149595, compound

HRID 2108605Notes

Reaction equation

HRID 2108605 reaction equation
C([O:9][C:10]1[CH:15]=[C:14]([I:16])[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH:26]([CH3:28])[CH3:27])[CH:19]=2)=[C:12]([I:29])[CH:11]=1)(=O)C1C=CC=CC=1.[OH-].[Na+].Cl>CO.O>[I:16][C:14]1[CH:15]=[C:10]([OH:9])[CH:11]=[C:12]([I:29])[C:13]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH:26]([CH3:27])[CH3:28])[CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25150328HCID 25150328, compound

Product 1

HCID 25149595HCID 25149595, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3,5-diiodo-4-(4′-methoxy-3′-iso-propylphenoxy)phenyl benzoate (0.10 g, 0.16 mmol) and 1 N NaOH (0.81 mL, 0.81 mmol) in methanol (1.63 mL) was at room temperature for 24 h. The reaction mixture was neutralized with 2 N HCl, diluted with H2O and extracted with CH2Cl2 (10 mL×2). The organic layers were concentrated under reduced pressure and the crude product was purified preparatory TLC with acetone-hexanes (1:4) as mobile phase to afford 3,5-diiodo-4-(4′-methoxy-3′-iso-propylphenoxy)phenol as an off-white solid (0.079 g, 95%): 1H NMR (300 MHz, DMSO-d6): δ 9.99 (s, 1H), 7.28 (s, 2H), 6.81 (d, J=12.0 Hz, 1H), 6.67 (d, J=3.0 Hz, 1H), 6.30 (m, 1H), 3.72 (s, 3H), 3.18 (m, 1H), 1.11 (d, J=6.9 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-acetone (7:3); Rf=0.42.

Workup

  1. extractionextracted with CH2Cl2 (10 mL×2)
  2. concentrationThe organic layers were concentrated under reduced pressure
  3. customthe crude product was purified preparatory TLC with acetone-hexanes (1:4) as mobile phase

Sources & evidence

ORD record
ord-8a96295830f14cbea010350e3c1d7207
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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