Hexahydrophthalic anhydride → HCID 2756601, compound

Participants

Reaction Steps

In a 2.5 l sulfuration flask equipped with a mechanical stirrer, thermometer and a refrigerator, 154.17 g (0.5 mol) of hexahydrophtalic anhydride are dissolved in 800 ml of benzene. The solution is cooled in an ice bath and 133.34 g (1.1 mol) of AlCl3 are added portion wise over one hour while maintaining the temperature between 0° C. and 5° C. When the addition is complete, the ice bath is removed and the reaction mixture is stirred for 2 hours at room temperature and subsequently heated to reflux during one hour. After cooling to room temperature, the reaction mixture is poured onto a mixture of ice and water while stirring with a mechanical stirrer. The precipitated product is filtered off and washed several times with water until the pH of the wash water is neutral. The material is dried in vacuum and the remaining product dissolved in chloroform. The solution is filtered over hyflo and the volume of the filtrate reduced in vacuum. The product precipitates as an off-white solid that is filtered off, washed with additional solvent and dried in vacuum. 66 g (57% yield) of the product are obtained as a white solid with a melting point of 130-132° C. 1H-NMR analysis is in agreement with the presence of a compound possessing the cis configuration of the substituents on the cyclohexane ring.

Provenance & Evidence