Chlorine → HCID 44140051, compound

Participants

Reaction Conditions

Reaction Steps

23.2 g (0.1 mol) of 2-benzoyl-cyclohexanecarboxylic acid and 100 ml of chorobenzene are heated to 55° C. while stirring. Chlorine gas is then slowly introduced into the suspension over two hours while maintaining the temperature at 58-60° C. When no more starting material is detected by thin layer chromatography (TLC) analysis, the slightly yellowish solution is purged with nitrogen during one hour and subsequently cooled to room temperature. The solvent is then distilled off in vacuum to give a yellowish oil which according to TLC analysis consists of two main products. These products are isolated via preparative column chromatography on silica gel, using white spirit/ethyl acetate 1:4 as the eluant. The first fraction isolated is obtained as white solid with a melting point of 89-92° C. and is identified by 1H-NMR and elemental analysis as 3a-chloro-3-hydroxy-3-phenyl-hexahydro-isobenzofuran-1-one 9.3 g (35% yield). The second fraction is obtained as viscous yellowish oil, which is identified by 1H-NMR and elemental analysis as 3,3a-dichloro-3-phenyl-hexahydro-isobenzofuran-1-one (6.7 g, 25% yield)

Provenance & Evidence