Introduction

Objective:

In this experiment, you will use standard synthetic laboratory techniques to carry out a multi-step synthesis of methyl diantilis.

Synthetic Scheme:

You will synthesize methyl diantilis using the synthetic scheme shown below.

You will start with ethylvanillin, a molecule commonly used in the production of chocolate. The ethyl vanillin will be reduced using sodium borohydride to produce 3-ethoxy-4-hydroxybenzyl alcohol. This intermediate species will then be reacted with methanol to produce methyl diantilis, a molecule that is commonly used to make perfumes and other fragrances.

The methanol in the second step of this reaction can be replaced by ethanol, propanol, or isopropanol in order to form ethyl, propyl, or isopropyl diantilis respectively. In this experiment, you will only be synthesizing methyl diantilis; however, the synthetic techniques are the same, and the NMRs of the other compounds will be provided for reference.