HCID 20745894, compound → HCID 20745895, compound

Participants

Reaction Steps

7.5 g (22.8 mmol) 5-[(6-chlorohexyl)oxy]isophthalic acid dimethyl ester (example 6) were dissolved in 75 ml ethyl acetate and charged into a steel autoclave. After addition of 3 g of a hydrogenation catalyst (5% Rh/Alox, Johnson Matthey Company) the vessel was closed and the compound was hydrogenated at a reaction temperature of 70° C. using a constant hydrogen pressure of 18 bar until no further hydrogen uptage was observed (approx. 4 hours). The reaction suspension was cooled to room temperature, filtered and concentrated under vacuum to dryness. The crude product was essentially a cis/trans mixture of 5-[(6-chlorohexyl)oxy]-1,3-cyclohexanedicarboxylic acid dimethyl ester. The pure cis-compound was isolated as a colourless oil by chromatography on silica gel using hexane/ethyl acetate (4:1) as eluent. (yield: 6.1 g, 80%).

Provenance & Evidence