Hydrochloric Acid → 3-(3,4,5-Trimethoxyphenyl)-2-(4-fluorophenyl)acrylic acid

Participants

Reaction Steps

A mixture of 4-fluoro phenyl acetic acid (2 g, 13 mmol), 3,4,5 trimethoxybenzaldehyde (2.5 g, 13 mmol), Ac2O (10 mL) and DIPEA (2.9 mL, 16.8 mmol) was stirred at room temperature for 12 hours. Upon completion, as monitored by TLC using DCM:MeOH (9:1) as the eluent, 10% aqueous HCl (10 mL) was added to the reaction mixture; the precipitate formed was filtered and dissolved in DCM (100 mL). The organic layer was washed with 10% aqueous NaOH (3×50 mL) and the basic aqueous solution was acidified with 10% aqueous HCl to pH 3. The precipitate formed was filtered, washed with 100 mL water and dried to get the product (2.4 g, 56% yield).

Provenance & Evidence