Formic Acid → Tricyclo [2.2.1.02,6]heptan-5-ol bisformate

Participants

Reaction Steps

To a stirred solution of 39.9 g paraformaldehyde in formic acid (800 ml) and conc. H2SO4 (15 ml) under nitrogen and at 20°C was added dropwise 132 g norbornadiene while keeping the temperature between 20°-25°C. After 1.5 hr the reaction was quenched by adding to 800 ml of ice-water. Extraction with ether (3 × 750 ml), washing the organic layer with water (1 × 250 ml), brine (3 × 250 ml) and drying (Na2SO4) afforded the crude 3-hydroymethyl tricyclo [2.2.1.02,6 ]heptan-5-ol bisformate (1') as an oil. Distillation, after a forerum of bp. 40°C/15mm, gave 235 g pure tricyclenebisformate, bp. 104°C/0.3 mm (84% yield).

Provenance & Evidence