4-Chlorobenzaldehyde → 4-[(4-Chlorobenzyl)oxy]benzaldehyde

Temperature

80 °C

In a 200-ml eggplant-type flask, 5.3 g (37.0 mmol) of 4-chlorobenzyl alcohol were weighed. After 80 ml of o-xylene, a nonpolar solvent, were added to form a solution, 28.0 g (37.0 mmol) of tetrakis[tris(dimethylamino)phosphoranilideneamino]phosphonium hydroxide was added to form a homogeneous solution. The solution was heated to 80° C., at which it was then maintained at 5 mmHg for 1 hour. Its pressure was allowed to rise back to normal pressure by nitrogen, followed by cooling to room temperature. Further, 50 ml of o-xylene and 5.20 g (37.0 mmol) of 4-chlorobenzaldehyde were added, followed by heating at 130° C. for 96 hours. The reaction mixture was washed four times with 100-ml portions of 1 N hydrochloric acid. The organic layer was separated and then concentrated to dryness. The residue was recrystallized from ethanol, whereby 5.6 g of 4-(4-chlorobenzyloxy)benzaldehyde were obtained as colorless crystals. Its isolation yield was 61%.

1. additionwas added
2. customto form a homogeneous solution
3. temperaturewas then maintained at 5 mmHg for 1 hour
4. temperatureby cooling to room temperature
5. temperatureby heating at 130° C. for 96 hours
6. washThe reaction mixture was washed four times with 100-ml portions of 1 N hydrochloric acid
7. customThe organic layer was separated
8. concentrationconcentrated to dryness
9. customThe residue was recrystallized from ethanol

ORD record

ord-8e00a46283014b658f47fa88f794b879

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06664365B2