State reaction with methyl magnesium bromide

Reference no: EM13174870

Compound A (C10H16O3) is insoluble in H2O, but soluble in bicarbonate solution. It yields a 2,4-dinitrophenylhydrazone derivative. Catalytic hydrogenation of Compound A, followed by Wolff-Kishner reduction, yields decanoic acid as the only organic product. Ozonolysis of Compound A (oxidizing conditions) yields Compound B (C8H14O3), which can be converted to octanoic acid by Wolff-Kishner reduction.

Compound B can also be prepared from cycloheptanone in 3 steps: reaction with methyl magnesium bromide, dehydration with phosphoric acid and ozonolysis followed by workup under oxidizing conditions.

Reference no: EM13174870

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