Water → (2-Benzyloxyphenyl)-p-tolylmethanol

In a nitrogen stream, an n-butyllithium hexane solution (2.44 M, 5.65 mL) was added dropwise to a solution of 1-benzyloxy-2-bromobenzene (3.3 g, 12.54 mmol) in THF (126 mL) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. To this mixture, a solution of 4-methylbenzaldehyde (1.28 g, 10.6 mmol) in THF (42 mL) was added at −78° C. The reaction mixture was stirred at the same temperature for one hour, and then water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)] to obtain the title compound (2.3 g, 71%).

1. stirringThe reaction mixture was stirred at the same temperature for one hour
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
4. dry with materialdried (anhydrous magnesium sulfate)
5. distillationthe solvent was distilled under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:5)]

ORD record

ord-6b38f605cdb542239dfdaa432642293c

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08048897B2