[CH3:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Na+].[I-:11].[OH-].[Na+].[O-]Cl.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].Cl>CO>[I:11][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[OH:9]To a stirred solution of 5.00 g (35.00 mmol) of 2-methyl-4-chlorophenol (available from Aldrich Chemical Company) in 100 mL of methanol at 0° C., add 6.83 g (45.57 mmol) of NaI and 1.40 g (35.00 mmol) of NaOH. To the resulting mixture add 65 mL of 5% aqueous NaOCl solution (commercial bleach) over one hour period. The resulting slurry is stirred for one more hour at 0° C. After the addition of 20 mL of 10% Na2S2O3 solution, the reaction mixture is acidified by dilute hydrochloric acid. The mixture is extracted with methylene chloride. The organic layer is washed with brine and dried over anhydrous magnesium sulfate. Removal of the solvent followed by purification by recrystallization from hexanes gives 3.80 g (40.5%) of (P11) as white solid.
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