反应详情

温度

70 °C

Then, 35.6 g of 4-bromo-2-ethyl-6-methyl-1-benzyloxybenzene was dissolved in 250 ml of tetrahydrofuran, and 69 ml of n-butyl lithium solution (in hexane; 1.69 mol/liter), while stirring at-70° C. After further stirring at 70° C. for 2 hours, a solution of 12.1 g of trimethoxyboron dissolved in 50 ml of tetrahydrofuran was added dropwise to the reaction mixture. After completion of the dropwise addition, the reaction mixture was returned to room temperature, stirred for 1 hour, and then poured into ice water. The mixture was made weak acidic by the addition of 10% hydrochloric acid, and extracted twice with 500 ml of diethyl ether. The ether layers was combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated to give a residue. To the residue was added 120 ml of toluene, and 33 ml of 30% aqueous hydrogen peroxide was added dropwise, while heating at 70° C. under stirring. After heating under reflux for 1 hours, the reaction mixture was returned to room temperature, washed once with water, twice with 10% aqueous ferrous ammonium sulfate and then once with water. The toluene layer was dried over anhydrous magnesium sulfate, and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 26.2 g of 3-ethyl-4-benzyloxy-5-methylphenol (93% yield).

1. additionwas added dropwise to the reaction mixture
2. additionAfter completion of the dropwise addition
3. customwas returned to room temperature
4. stirringstirred for 1 hour
5. extractionextracted twice with 500 ml of diethyl ether
6. washwashed with water
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated
9. customto give a residue
10. additionwas added dropwise
11. temperaturewhile heating at 70° C.
12. stirringunder stirring
13. temperatureAfter heating
14. temperatureunder reflux for 1 hours
15. customwas returned to room temperature
16. washwashed once with water, twice with 10% aqueous ferrous ammonium sulfate
17. dry with materialThe toluene layer was dried over anhydrous magnesium sulfate
18. concentrationconcentrated
19. customto give a crude product