Place 10 mmoles of cyclohexanol and a stir bar in an Erlenmeyer flask. Place over a
stir motor and stir while you carefully add 2.5 mL of acetic acid (conc.). Place
15 mL of bleach (approximately 5.25% sodium hypochlorite*) in your separatory
funnel, position the separatory funnel above the Erlenmeyer flask, and add the
bleach dropwise to the cyclohexanol/acetic acid mixture. The addition of bleach
should take about 15 min. If the reaction flask becomes hot to the touch during the
bleach addition, use an ice bath to cool it down. When the addition of the bleach is
complete, the solution will be pale yellow to yellow-green in color. Test the solution
for excess hypochlorous acid and, if necessary, add additional bleach.
Stir the reaction mixture for an additional 15 min at room temperature. Then,
quench excess oxidant by adding about 0.5 mL of saturated sodium bisulfite solu-
tion.
† Test for excess hypochlorous acid and, if necessary, add additional sodium
bisulfite.
Add 2 drops of thymol blue (an indicator), then add 6N NaOH until the solution is
just basic. Add solid NaCl until the solution is saturated with salt, then decant the
liquid into your separatory funnel. Extract with 5 mL of methylene chloride, save
the organic layer, then extract the aqueous layer one more time with 5 mL of meth-
ylene chloride.