R. B. Woodward was one of the leading organic chemists of the middle part of the twentieth century. Known primarily for his achievements in the synthesis of complex natural products, he was awarded the Nobel Prize in chemistry in 1965. He entered Massachusetts Institute of Technology as a 16-year-old freshman in 1933 and four years later was awarded the Ph.D. While a student there he carried out a synthesis of estrone, a female sex hormone. The early stages of Woodward’s estrone synthesis required the conversion of m-methoxybenzaldehyde to m-methoxybenzyl cyanide, which was accomplished in three steps:
Suggest a reasonable three-step sequence, showing all necessary reagents, for the preparation of m-methoxybenzyl cyanide from m-methoxybenzaldehyde.
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