Benzene, (2,2-dimethylpropyl)- → 4-(2,2-Dimethylpropyl)benzaldehyde

Temperature

0 °C

(2,2-Dimethylpropyl)benzene (9.33 g, 63 mmol) was dissolved in dichloromethane (50 mL) and cooled to 0° C. on an ice bath. With vigorous stirring, SnCl4 (28.66 g, 110 mmol) was added all at once via syringe, followed by dropwise addition of dichloromethyl methyl ether (7.24 g, 63 mmol) over 10 min. After 20 min, the ice bath was removed, and the mixture was quenched by the addition of ice-water (100 mL). The aqueous layer was discarded and the organic phase was washed with water (3×25 mL), 3 N hydrochloric acid (3×25 mL), and aqueous saturated sodium chloride (2×25 mL). The organic phase was then treated with activated carbon, dried (magnesium sulphate), filtered and concentrated in vacuo. This afforded the title compound. Yield 7.49 g (62%).

1. customthe ice bath was removed
2. customthe mixture was quenched by the addition of ice-water (100 mL)
3. washthe organic phase was washed with water (3×25 mL), 3 N hydrochloric acid (3×25 mL), and aqueous saturated sodium chloride (2×25 mL)
4. additionThe organic phase was then treated with activated carbon
5. dry with materialdried (magnesium sulphate)
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-5e1060fdd64747fba900430ca4d8ba21

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06762318B2