Provide a 6 step synthetic route for the following transformation. 6 Steps OEt

Question

Question

Answer 1

Answer #1

The product which is a tertiary alcohol, can be synthesized if we have an ester of propionic acid and phenylmagnesium bromide.

LiAlH4 PBr3 ABO NaCN OH -CN OEt HCI, H2O i . OYOY OH OET LOH 1. PhMgBr EtOH 2. H30 H2SO4 (cat)

Step 1: Conversion of ethyl acetate to ethanol using LiAlH₄ reduction.

Step 2: Conversion of ethanol to ethyl bromide using PBr₃.

Step 3: Conversion of ethyl bromide to propane nitrile using sodium cyanide.

Step 4: Conversion of propane nitrile to propionic acid by aqueous acidic hydrolysis.

Step 5: Conversion of propionic acid to ethyl propionate using ethanol in presence of sulfuric acid.

Step 6: Reaction of ethyl propionate with phenylmagnesium bromide and subsequent aqueous acidic work up gives the product.

Answer 2

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