Acetic Acid → HCID 19786906, compound

Participants

Reaction Steps

A solution of malonic acid (Aldrich, 4.36 g, 41.9 mmol), 3,5-di-tert-butyl-4-hydroxybenzaldehyde (Aldrich, 5.00 g, 20.9 mmol), piperidine (Aldrich, 0.18 g, 2.10 mmol) and acetic acid (0.13 g, 2.10 mmol) in toluene (100 mL) was warmed at reflux (water removed using a Dean-Stark trap). After 5.5 h malonic acid was added (4.36 g, 41.9 mmol) and the reaction mixture was warmed at reflux for 12 h. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was chromatographed (SiO2, flash, methanol-methylene chloride, 5:95) to give 2.43 g (42.1% yield of (E)-1-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl propenoic acid as a white solid.

Provenance & Evidence