>>14401810REACTION 3: SYNTHESIS OF 2-(3-METHOXYPHENYL)-2-HYDROCYCLOHEXANE-1-ONE (YIELD ? 85%)
a. The 1-(3-methoxyphenyl)-cyclohexene (14.40 g, 75 mmol), synthesized in the 2nd reaction, was added to a mixture of 150 mL deionized water and 370 mL acetone
b. Acetic acid (12.5 mL) was added to the reaction mixture, and the combined mixture was stirred for 45 min at standard conditions
c. While the reaction mixture stirred, a solution of KMnO4 (16.60 g, 105 mmol) was prepared in 37.5 mL of deionized water and 150 mL of acetone
d. While maintaining continuous stirring at standard conditions, the solution was added dropwise to the reaction mixture, and the combined reaction mixture was allowed to stir for an additional 1 hour
e. While the reaction mixture stirred, a solution of sulfuric acid:deionized water was prepared in a 75:600 ratiod
f. While maintaining continuous stirring at standard conditions, the solution was added slowly to the reaction mixture, and the combined reaction mixture was stirred for an additional 30 minutes
g. While maintaining continuous stirring at standard conditions, sodium nitrite (10.20 g, 120 mmol) was added to the reaction mixture, and the combined reaction mixture was stirred for 30 min h. 800 mL of diethyl ether was added to the reaction mixture
i. The organic layer was neutralized with sodium hydroxide, separated, and dried over magnesium sulfate
j. The solvent was allowed to evaporate, generating 2-(3-methoxyphenyl)-2-hydroxycyclohexane-1-one as a crude product
k. The crude product was purified by silica gel column chromatography using a 20:3 mixture of hexane and ethyl acetate, resulting in a yellow liquid
