R. B. Woodward was one of the leading organic chemists of the middle part of the twentieth
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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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