Water → 3,4-Di(methoxymethoxy)styrene

Participants

Reaction Steps

A solution of CH3PPh3Br (10.72 g, 30 mmol) in anhydrous DMF (50 mL) under argon atmosphere was cooled to 0-5° C. Sodium hydride (2.0 g, 60% suspension in mineral oil, 50 mmol, 1.66 eq.) was added in portions. The mixture was stirred at room temperature for 1 hour and then 3,4-di-(methoxymethoxy)-benzaldehyde (6 g, 26.52 mmol) was added in portions. The resulting mixture was stirred at room temperature until completion of the reaction (about 2 hours). The mixture was cooled again to 0-5° C. and water (5 mL) was slowly injected to decompose the excess NaH. After an additional 10 min, the mixture was mixed with water (200 mL) and extracted with CH2Cl2 (2×200 mL). The organic layer was washed with water (200 mL), dried over anhydrous sodium sulfate, filtered and evaporated. The residue was mixed with hexanes and loaded to a silica gel column that was eluted with a mixed solvent of hexane and EtOAc to afford, after evaporation, 3.974 g of 3,4-di(methoxymethoxy)styrene as a yellowish oil (17.72 mmol, yield 66.8%). MS (ESI) m/z: 225 (M+1)+ and 247 (M+23)+.

Provenance & Evidence