Dimethylformamide → 4-(Butoxymethyl)benzaldehyde

Temperature

-78 °C

To a solution of 1-bromo-4-butoxymethyl-benzene (11.5 g, 47.3 mmol) described in Manufacturing Example 4-1-1 in tetrahydrofuran (200 mL) was added n-butyl lithium (32.5 mL, 1.6 M hexane solution, 52.0 mmol) at −78° C. This mixture was stirred for 55 minutes at −78° C., and N,N-dimethylformamide (4.4 mL, 56.8 mmol) was added thereto at −78° C. This mixture was warmed to room temperature, and stirred for 20 minutes. The reaction solution was partitioned into water and ethyl acetate at 0° C. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (7.39 g, 81%).

1. customat −78° C
2. temperatureThis mixture was warmed to room temperature
3. stirringstirred for 20 minutes
4. customThe reaction solution was partitioned into water and ethyl acetate at 0° C
5. washThe organic layer was washed with saturated aqueous sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent was evaporated under a reduced pressure
8. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=10:1)

ORD record

ord-6cd975db1296411eb86b6abb212f81cc

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153662B2