Hydrochloric Acid → HCID 68406476, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methylphenylacetic acid (3 g, 20 mmol) and methyl 4-formylbenzoate (3.3 g, 20 mmol) was dissolved under stirring with Ac2O (8 mL). To this mixture, diisopropylethylamine (DIPEA) (5.2 mL, 30 mmol) was added and stirred at 30° C. for 6 hours. Upon completion, as monitored by TLC using 100% ethyl acetate as eluent, the reaction mixture was poured into water and pH was adjusted to 3 using aqueous dilute HCl (1:1). The aqueous layer was extracted with ethyl acetate (2×150 mL). The combined ethyl acetate layer was washed with water till the washings were neutral and dried over anhydrous Na2SO4. The ethyl acetate layer was evaporated to dryness to obtain a sticky compound, which was triturated with cold dichloromethane (DCM) to furnish a pale yellow solid. It was filtered and dried under vacuum to afford the title compound (3.88 g, 66% yield).

Provenance & Evidence