Acetic Acid → (5-Bromo-2-methylphenyl)methanol

Temperature

17.5 °C

161.2 g (810 mmol) of 5-bromo-2-methylbenzaldehyde was dissolved in 1.5 L of tetrahydrofuran and 150 ml of water, and to the resulted solution was dropped, at 15 to 20° C., a solution prepared by dissolving 10.0 g (264 mmol) of sodium boron hydride in 100 ml of a 0.1 wt % sodium hydroxide aqueous solution. After completion of dropping, the mixture was stirred at 15 to 20° C. for 4 hours. To the reaction solution was dropped 12.0 g of glacial acetic acid at 20° C. or lower, then, this was poured into ice water. The reaction solution was extracted with t-butyl methyl ether, the organic layer was washed with water, further washed twice with a saturated sodium bicarbonate solution, then, washed with saturated saline, and dried over anhydrous magnesium sulfate, then, concentrated to obtain 168 g of 5-bromo-2-methylbenzyl alcohol.

1. customa solution prepared
2. extractionThe reaction solution was extracted with t-butyl methyl ether
3. washthe organic layer was washed with water
4. washfurther washed twice with a saturated sodium bicarbonate solution
5. washwashed with saturated saline
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated

ORD record

ord-d540d75667754b1399a43f0c7522fa10

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06762197B2