The oxidation of a primary alcohol to the corresponding carboxylic acid via permanganate and phase-transfer catalyst has been modified to circumvent impurity formation incurred during the reaction. A safe, simple, and efficient process was developed which gave the required carboxylic acid in 77% isolated yield using sodium permanganate in the presence of tetraethylammonium hydrogen sulphate.
The catalytic dicuprate addition of 1,9-dibromononane to a sterol 1,6-dienone is strongly enhanced by the presence of dimethylsulfide. Dimethylsulfide appears to have an important stabilising effect on the active organo-dicuprate species formed by reaction of Cu(I)Cl with di(bromomagnesio)nonane. In the absence of dimethlysulfide, 1,2-addition of the Grignard and loss of acetate from the sterol are the dominant processes. The overall reaction yield is also very sensitive to the order of addition of various reagents, with controlled addition of the preformed Grignard reagent to a dienone/Cu(I)Cl/dimethyl sulfide mixture leading to high yields of the desired alkylated bis-enone.
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