4-(4-Methoxy-3-methylphenyl)butan-1-ol → 4-Methoxy-3-methylbenzenebutanoic acid

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 1.7 grams (0.009 mole) of 4-(4-methoxy-3-methylphenyl)butan-1-ol in 50 mL of acetone was cooled to 0° C.-4° C., and about 15 to 20 mL (excess) of Jones Reagent was added dropwise. Upon completion of addition, the reaction mixture was stirred at 0° C. for two hours, then it was allowed to warm to ambient temperature, where it stirred for an additional three hours. After this time, the reaction mixture was diluted with isopropanol and filtered. The filter cake was washed with acetone, and the combined filtrate and wash were concentrated under reduced pressure to a residue. The residue was partitioned with methylene chloride and water and the separated organic layer was washed with water. The organic layer was then dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was dried under vacuum, yielding 1.1 grams of subject compound. The NMR spectrum was consistent with the proposed structure. The reaction was repeated to obtain an additional amount of subject compound.

Provenance & Evidence