Water → HCID 10634202, compound

Temperature

-50 °C

To a solution of 2-(2,4-dichlorophenyl)-1,3-dioxolane (31.9 g) in tetrahydrofuran (220 ml) was added dropwise 1.6M n-butyllithium in hexane (110 ml) at -60 to -50° C. in a dry ice-acetone bath, and the mixture was stirred at -50° C. After 1 hour, to the reaction mixture was added N,N-dimethylformamide (56.4 ml). After 15 minutes, the mixture was stirred at ambient temperature for 1 hour then water (200 ml) was added thereto. The mixture was extracted with ethyl acetate (100 ml) twice, the organic layer was washed with water 3 times, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash silica gel chromatography eluted with n-hexane-ethyl acetate (10:1, V/V) and crystallized with diisopropyl ether to give 2,6-dichloro-3-(1,3-dioxolan-2-yl)benzaldehyde (4.91 g) as colorless crystals.

1. waitAfter 15 minutes
2. stirringthe mixture was stirred at ambient temperature for 1 hour
3. extractionThe mixture was extracted with ethyl acetate (100 ml) twice
4. washthe organic layer was washed with water 3 times
5. dry with materialdried over magnesium sulfate
6. customevaporated in vacuo
7. customThe residue was purified by flash silica gel chromatography
8. washeluted with n-hexane-ethyl acetate (10:1, V/V)
9. customcrystallized with diisopropyl ether

ORD record

ord-a21a0b9ec8284775988951e3b334d096

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06008229