3-Pyridinemethanol → 2-(p-Isobutylphenyl)propionic acid-3-pyridylmethyl ester

Participants

Reaction Steps

A mixture of 0.05 g of sodium and 8 ml of 3-hydroxymethylpyridine was heated at 65°-70° C. for 10 hours. To this mixture was added 3.8 g of 2-(p-isobutylphenyl)propionic acid methyl ester, and the whole was heated at 95°-100° C. for 8 hours. After cooling to room temperature, 100 ml of water was added. The resulting mixture was extracted with ether, and the ether was distilled away from the extract to leave a residue. The residue was passed through a column of silica gel, and the adsorbate was eluted with chloroform. The eluates were freed of chloroform in vacuo to give 2.9 g of 2-(p-isobutylphenyl)propionic acid-3-pyridylmethyl ester as a colorless oil. The infrared spectrum showed strong C=O absorption at 1730 cm-1 characteristic for ester. Mass spectrum: parent ion 297 m/e.

Provenance & Evidence