Heptane → 1,2,2-Trimethyl-1,3-cyclopentanedicarboxylic acid

Participants

Reaction Steps

Cocrystals of dimethyl fumarate and (+)-camphoric acid were prepared as follows. 36 mg of dimethyl fumarate and 200 mg of (+)-camphoric acid were combined in an agate jar with a 4 ml capacity. One drop of 1:3 (v:v) ethyl acetate:heptane was added along with two agate grinding balls. The mixture was milled for 60 minutes at full power on a Retch mm2 mixer mill. The starting concentrations of dimethyl fumarate and (+)-camphoric acid were chosen such that the thermodynamically stable solid phase at equilibrium is the cocrystal of dimethyl fumarate and (+)-camphoric acid. The crystalline material that formed was isolated to yield the dimethyl fumarate: (+)-camphoric acid (1:4, by NMR) cocrystal. The measured melting points were 103±1° C. for dimethyl fumarate, 185±2° C. for (+)-camphoric acid, and 88±2° C. for the cocrystal.

Provenance & Evidence