Hydrochloric Acid → (4-Bromo-3-methylphenyl)methanol

Temperature

-20 °C

10.55 g of methyl 4-bromo-3-methylbenzoate was dissolved in 110 mL of tetrahydrofuran, to which 1.31 g of lithium aluminium hydride was added dropwise in small portions at −30 to −20° C., and this mixture was stirred for 15 minutes at −20° C. Then a mixed solution of methanol and water (4:1) was added dropwise to the reaction mixture, and this mixture was stirred for 30 minutes at room temperature. The reaction mixture, to which water was added, was adjusted to pH 7 with 6M hydrochloric acid followed by addition of ethyl acetate, and the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 9.20 g of (4-bromo-3-methylphenyl)methanol as brown oil.

1. additionwas added dropwise in small portions at −30 to −20° C.
2. stirringthis mixture was stirred for 30 minutes at room temperature
3. customthe organic phase was separated
4. washAfter the resultant organic phase was washed with water
5. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
6. distillationthe solvent was distilled out under reduced pressure

ORD record

ord-3039f072d6724b5bae963201e648984f

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772285B2