HCID 19760432, compound → HCID 19760419, compound

Participants

Reaction Conditions

Reaction Steps

A 1-L stainless steel autoclave was charged with 100 g of oxydi(3,4-dicarbomethoxybenzene), 3.00 g of 5% rhodium on alumina, and 750 mL of THF. With stirring, the reactor was purged several times with hydrogen and then charged to approximately 2000 psi of hydrogen. The reaction mixture was heated to 120° C., and the mixture was allowed to stir for 20 h. The reactor was cooled and vented, and the crude reaction mixture removed. The solution was filtered to remove catalyst and then concentrated using a rotary evaporator. The oily residue was partitioned between water and ethyl acetate. The organic phase was washed with brine, dried (MgSO4), and concentrated to a clear lightly colored oil using a rotary evaporator. Gas chromatographic analysis of the crude product reveals a mixture of tetramethyl oxydi(cyclohexane-3,4-dicarboxylate) (major), dimethyl cyclohexanedicarboxylate (minor), and dimethyl 4-hydroxycyclohexanedicarboxylate (minor).

Provenance & Evidence