Sodium Chloride → Bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate

Participants

Reaction Conditions

Reaction Steps

A two-phase mixture of 70% aqueous tert-butyl hydroperoxide (103.9 grams, 807 mmol), cyclohexane (200 ml) and sodium chloride (15 grams) is shaken in a separatory funnel. The organic phase is dried over anhydrous magnesium sulfate, filtered and added to 40 grms (101 mmol) of bis(2,2,6,6-tetramethylpiperidin-4-yl) succinate. Molybdenum trioxide (2.0 grams) is added and the mixture is heated at reflux for one hour. Water is collected in a Dean-Stark trap. The entire reaction mixture is then transferred to a Fischer-Porter pressure bottle and heated for six hours at 140° C. Additional tert-butyl hydroperoxide (90%, 10.1 grams, 101 mmol) is added and heating is resumed for another four hours. The colorless reaction mixture is filtered, concentrated and dissolved in heptane (200 ml). The heptane solution is passed through a column of silica gel with heptane as the eluent to obtrain 41.2 grams (69% yield) of bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) succinate as a white solid melting at 122-126° C. Further elution of the column with 10:1 heptane:ethyl acetate affords the title compound as a mixture of cyclohexanediyl isomers.

Provenance & Evidence