4-iodo-3,5-dimethylphenol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 0-Benzyl-3,5-dimethyl-4-iodophenol was prepared as follows: In a 500 ml round-bottom flask were placed 30.0 g (121 mmol) of 3,5-dimethyl-4-iodophenol, 190 ml acetone, 16.9 g (122 mmol) potassium carbonate and 20.7 g (121 mmol) benzyl bromide. The mixture was refluxed for 15 hours, cooled, filtered and the precipitate washed with acetone. The combined filtrate was evaporated under reduced pressure to yield an orange oil which slowly crystallized. This was dissolved in methylene chloride and water and the methylene chloride layer sequentially washed with 5% sodium hydroxide, saturated sodium bisulfite and water. After drying over magnesium sulfate and filtering, the methylene chloride was removed under reduced pressure. The resulting solid was recrystallized from hot methanol, cooled to room temperature and then in ice, collected and washed with cold methanol to yield 27.9 g (68% yield) of white plates, mp 56-57, which were identified as O-Benzy13,5-dimethyl-4-iodophenol. 1H NMR analysis indicated: (δ, CDCl3) 7.68 (m, 5H), 6.62 (s, 2H), 4.88 (s, 2H) and 2.39 (s, 6H). Mass spectrum analysis indicated: (m/e) 338 (M+) and 91. In a 500 ml round-bottom flask were placed The mixture was refluxed for 15 hours cooled filtered the precipitate washed with acetone The combined filtrate was evaporated under reduced pressure to yield an orange oil which slowly crystallized This was dissolved in methylene chloride water and the methylene chloride layer sequentially washed with 5% sodium hydroxide, saturated sodium bisulfite and water After drying over magnesium sulfate filtering the methylene chloride was removed under reduced pressure The resulting solid was recrystallized from hot methanol in ice, collected washed with cold methanol to yield 27.9 g (68% yield) of white plates, mp 56-57, which

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: O-Methyl-3,5-dimethyl-4-iodophenol was prepared by etherifying 3,5-dimethyl-4-iodophenol as follows: In a 1 l three-necked flask equipped with an overhead stirrer were placed 63.7 g (257 mmol) of 3,5-dimethyl-4-iodophenol, 70.9 g (513 mmol) potassium carbonate, 400 ml acetone and 47.5 ml (108 g, 760 mmol) methyl iodide. The reaction mixture was refluxed for 15 hours, cooled, the precipitate filtered and washed with acetone. The combined acetone washes were concentrated under reduced pressure, dissolved in methylene chloride, washed successively with 5% sodium hydroxide, saturated sodium bisulfite and water. After drying over magnesium sulfate and filtering, the solvent was removed under reduced pressure to afford a tan oil. Recrystallization from hot methanol with cooling to room temperature and then -78° C. afforded 58.2 g (86% yield) of white needles, mp 33°-34° C., which were identified as O-methyl-3,5-dimethy-4-iodophenol. 1H NMR analysis indicated: (δ, CDCl3) 6.56 (s, 2H), 3.67 (s, 3H) and 2.37 (s, 6H). Mass spectrum analysis indicated: (m/e) 262 (m+, 100%), 247, 219, 135 and 91. In a 1 l three-necked flask equipped with an overhead stirrer The reaction mixture was refluxed for 15 hours cooled the precipitate filtered washed with acetone The combined acetone washes were concentrated under reduced pressure dissolved in methylene chloride washed successively with 5% sodium hydroxide, saturated sodium bisulfite and water After drying over magnesium sulfate filtering the solvent was removed under reduced pressure to afford a tan oil Recrystallization from hot methanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3,5-dimethyl-4-iodophenol was prepared as follows: To a solution of 59.1 g (484 mmol) of 3,5-dimethylphenol in 1 l of methanol was added 395 ml of 36% hydrochloric acid, with occasional cooling to maintain the temperature at 20°-30° C. To the resulting solution was then added a solution of 54.3 g (327 mmol) potassium iodide and 33.5 g (157 mmol) potassium iodate in 500 ml water over a 5 minute period. The solution became red and cloudy and a tan precipitate formed. After stirring at room temperature for 20 hours, the reaction mixture was cooled in ice and the precipitate collected and washed with ice cold 2/1 (v:v) water/methanol. The resulting tan solid was recrystallized several times from hot methanol and water to yield 36.4 g (15% yield) of white needles, mp 131°-132° C., which were identified as 3,5-dimethyl-4-iodophenol. 1H NMR analysis indicated the following: (δ, CDCls) 8.03 (br s, lH), 6.52 (s, 2H) and 2.35 (s, 6H). Mass spectrum analysis indicated the following: (m/e) 248 (m+, 100%), 121, 91 and 77. with occasional cooling to maintain the temperature at 20°-30° C cloudy and a tan precipitate formed the reaction mixture was cooled in ice the precipitate collected washed with ice cold 2/1 (v:v) water/methanol The resulting tan solid was recrystallized several times from hot methanol and water