Isophthalaldehyde → 3-Vinylbenzaldehyde

To a suspension of methyltriphenylphosphonium bromide (27.2 g) in THF (200 mL) at 0° was added dropwise n-butyllithium (47 mL of 1.6M in hexane). The reaction mixture was stirred 30 min at 0° and cooled to -10°. The reaction mixture at -10° was transferred dropwise through a canula to a solution of isophthalaldehyde (10.0 g) in THF (300 mL) at -50°. The reaction was allowed to warm up to room temperature. After 3.5 hours at room temperature the reaction mixture was quenched with NH4OAc buffer (200 mL). The reaction mixture was extracted with ethyl acetate, dried over sodium sulfate and evaporated. Flash chromatography of the residue starting with 10% and finishing with 15% of diethyl ether in hexane afforded the title compound.

1. temperaturecooled to -10°
2. customat -10°
3. customAfter 3.5 hours at room temperature the reaction mixture was quenched with NH4OAc buffer (200 mL)
4. extractionThe reaction mixture was extracted with ethyl acetate
5. dry with materialdried over sodium sulfate
6. customevaporated

ORD-Eintrag

ord-338225b17c69438bb9afb8a932a6624b

Quelldatensatz

uspto-grants-1995_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05428171