cyclohexane-1,3,5-triol

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 1.32 g (10 mmol) of cyclohexane-1,3,5-triol (a mixture of cis- and trans-isomers) dissolved in 20 ml of pyridine was added dropwise 6.51 g (45 mmol) of 3-cyclohexene carbonyl chloride within 30 minutes at 5° C. or lower, followed by stirring at 0 to 5° C. for 4 hours to allow the reaction to proceed. After the reaction, the reaction solution was poured into a mixture of 50 ml of 10% hydrochloric acid and 50 ml of ice water, and the resultant was extracted with 30 ml of chloroform three times. The combined organic layers were washed twice with 30 ml of saturated sodium bicarbonate solution and then with 30 ml of saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4.6 g of the desired 1,3,5-tris(3-cyclohexene carbonyloxy)cyclohexane as a pale yellow oil. the reaction After the reaction the resultant was extracted with 30 ml of chloroform three times The combined organic layers were washed twice with 30 ml of saturated sodium bicarbonate solution with 30 ml of saturated sodium chloride solution and dried over anhydrous magnesium sulfate The solvent was removed under reduced pressure