4-iodo-2-methoxyphenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Iodo-2-methoxyphenol was prepared according to the method described by K. J. Edgar and N. Falling, J. Org. Chem. 55, 5287 (1990). Guaiacol (50.0 g, 402 mmol), sodium iodide (60.5 g, 402 mmol) was dissolved in methanol (800 ml) and cooled to 0° C., and sodium hydroxide (16.0 g, 402 mmol) was added at such a rate that the temperature did not exceed 5° C. An aqueous solution of sodium hypochlorite (750 ml, 72% solution, 402 mmol) was added during 45 min. The temperature was not allowed to exceed 0° C. After completed addition it was stirred for another 10 minutes at 0° C. First aqueous hydrochloric acid (100 ml, 4 M solution) and then sodium sulifite (200 ml saturated aqueous solution) was added. The product was extracted with ether was followed by drying over magnesium sulfate. Evaporation of the solvent was followed by distillation and the fraction at 105-106° C. at 0.1 mm Hg was collected. Yield 55 g, 54%. did not exceed 5° C to exceed 0° C addition it The product was extracted with ether by drying over magnesium sulfate Evaporation of the solvent was followed by distillation the fraction at 105-106° C. at 0.1 mm Hg was collected

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-iodo-2-methoxyphenol (90 g) in DMF (450 mL) were added K2CO3 (60 g) and 4-ethylbenzyl chloride (58 g) at RT. The reaction mixture was stirred at 80° C. for 3 hr. Water (900 mL) was added to the reaction mixture. The precipitated solid was collected on a filter and dried under reduced pressure. The suspension of this solid in heptane (520 mL) was stirred at RT. The precipitated solid was collected on a filter and dried under reduced pressure to give the title compound (115 g, 87%). The precipitated solid was collected on a filter dried under reduced pressure The suspension of this solid in heptane (520 mL) was stirred at RT The precipitated solid was collected on a filter dried under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (4-cyclopropylphenyl)methanol (4.5 g) prepared in (2) and 4-iodo-2-methoxyphenol (7.5 g) in THF (40 mL) were added triphenylphosphine (8.7 g) and diisopropyl azodicarboxylate (6.5 mL) at 0° C. The reaction mixture was stirred at RT for 22 hr. The solvent was removed under reduced pressure. The residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1) to give the title compound (5.3 g, 46%). The solvent was removed under reduced pressure The residue was purified by silica-gel chromatography (Developing solvent: hexane/ethyl acetate=9/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Iodo-2-methoxyphenol was prepared according to the method described by K. J. Edgar and N. Falling, J. Org. Chem. 55, 5287 (1990). Guaiacol (50.0 g, 402 mmol), sodium iodide (60.5 g, 402 mmol) was dissolved in methanol (800 ml) and cooled to 0° C., and sodium hydroxide (16.0 g, 402 mmol) was added at such a rate that the temperature did not exceed 5° C. An aqueous solution of sodium hypochlorite (750 ml, 7.2% solution, 402 mmol) was added during 45 min. The temperature was not allowed to exceed 0° C. After completed addition it was stirred for another 10 minutes at 0° C. First aqueous hydrochloric acid (100 ml, 4 M solution) and then sodium sulfite (200 ml saturated aqueous solution) was added. The product was extracted with ether was followed by drying over magnesium sulfate. Evaporation of the solvent was followed by distillation and the fraction at 105-106° C. at 0.1 mm Hg was collected. Yield 55 g, 54%. did not exceed 5° C to exceed 0° C addition it The product was extracted with ether by drying over magnesium sulfate Evaporation of the solvent was followed by distillation the fraction at 105-106° C. at 0.1 mm Hg was collected

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Iodo-2-methoxyphenol was prepared according to the method described by K. J. Edgar and N. Falling, J. Org. Chem. 55, 5287 (1990). Guaiacol (50.0 g, 402 mmol), sodium iodide (60.5 g, 402 mmol) was dissolved in methanol (800 ml) and cooled to 0° C., and sodium hydroxide (16.0 g, 402 mmol) was added at such a rate that the temperature did not exceed 5° C. An aqueous solution of sodium hypochlorite (750 ml, 72% solution, 402 mmol) was added during 45 min. The temperature was not allowed to exceed 0° C. After completed addition it was stirred for another 10 minutes at 0° C. First aqueous hydrochloric acid (100 ml, 4 M solution) and then sodium sulifite (200 ml saturated aqueous solution) was added. The product was extracted with ether was followed by drying over magnesium sulfate. Evaporation of the solvent was followed by distillation and the fraction at 105-106° C. at 0.1 mm Hg was collected. Yield 55 g, 54%. did not exceed 5° C to exceed 0° C addition it The product was extracted with ether by drying over magnesium sulfate Evaporation of the solvent was followed by distillation the fraction at 105-106° C. at 0.1 mm Hg was collected