Methanol → Tricyclo(3.3.1.13,7)decane-1-carboxylic acid, methyl ester

Participants

Reaction Steps

A mixture of 1-adamantanecarboxylic acid (572 gm.), methanol (2.2 liters), and H2SO4 (90 ml.) was refluxed 5 hours and then cooled to room temperature overnight. The reaction mixture was poured into 28 liters of water and extracted with chloroform (2 × 150 ml. for each 3.5 liters of solution). The chloroform extracts were combined, washed with water, dried, and concentrated. The residual oil was distilled to give 476 gm. product (77.5% yield) b17 approx. 143°.

Provenance & Evidence