1-Butanol → 4-Butoxymethyl-benzonitrile

To a mixture of sodium hydride (270 mg, 11 mmol, 66% in oil) and tetrahydrofuran (20 mL) was added n-butanol (1.1 mL, 12 mmol) at 0° C., which was stirred for 45 minutes at room temperature. The reaction mixture was cooled to 0° C., and a mixture of 4-cyanobenzyl bromide (1.5 g, 7.4 mmol) and tetrahydrofuran (10 mL) was added dropwise at that temperature. The reaction mixture was stirred for 3 hours at room temperature, and N,N-dimethylformamide (10 mL) was added to the reaction mixture and stirred for further 4.5 hours at the same temperature. The reaction mixture was partitioned into water and diethyl ether. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:6) to obtain the title compound (1.2 g, 84%).

1. temperatureThe reaction mixture was cooled to 0° C.
2. additionwas added dropwise at that temperature
3. stirringThe reaction mixture was stirred for 3 hours at room temperature
4. stirringstirred for further 4.5 hours at the same temperature
5. customThe reaction mixture was partitioned into water and diethyl ether
6. washThe organic layer was washed with saturated aqueous sodium chloride
7. customthe solvent was evaporated under a reduced pressure
8. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:6)

ORD record

ord-09790ed201ee4db28e1a663cb3446264

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2