A student attempted the following synthesis of - methoxy- benzyl alcohol from o-cresol, but got essentially no yield. What went wrong?

In this problem, the reactants are o-cresol and an unknown reagent used for the synthesis of the desired product - methoxy-benzyl alcohol. Let's first write the structures of o-cresol and methoxy-benzyl alcohol. o-Cresol: \(\ce{(CH3)C6H4(OH)}\) Methoxy-benzyl alcohol: \(\ce{C7H8O2}\)

To synthesize methoxy-benzyl alcohol from o-cresol, we need to substitute the methyl group (CH3) on the benzene ring with an -CH2OH group. This can be done by using a benzyl alcohol derivative as the reagent. The reagent that should be used for the synthesis of methoxy-benzyl alcohol is benzyl alcohol (\(\ce{C6H5CH2OH}\)).

The given synthesis has mentioned that the student used o-cresol to synthesize methoxy-benzyl alcohol, but essentially got no yield. This suggests that something went wrong in the synthesis process. The problem is likely in the reagent used or the reaction conditions. Without more information, we cannot determine the exact issue or reason for the low yield. However, we can give some general advice on how to improve the synthesis.

Here are a few potential improvements that could be made to the synthesis to increase the yield of methoxy-benzyl alcohol: 1. Ensure that the correct reagent (benzyl alcohol) is being used for the synthesis. 2. Optimize the reaction conditions, such as temperature, pressure, and concentration of the reactants, to facilitate the desired reaction and increase the yield. 3. Use a suitable catalyst to speed up the reaction and reduce the risk of side reactions occurring. 4. Evaluate the purification and isolation techniques used to recover the product, as inefficient methods can result in low yields. With these considerations in mind, the student should attempt the synthesis again and potentially achieve a higher yield of methoxy-benzyl alcohol from o-cresol.