I will be performing a synthesis in lab using this scheme except p-TsOH and CH2C
ID: 955716 • Letter: I
Question
I will be performing a synthesis in lab using this scheme except p-TsOH and CH2Cl2 my TA told me to use HoAc and EtOH instead. I will only be given two grams of starting material. We will be doing the reaction over the span of 2 weeks but my TA said depending on your reaction you may be able to complete the steps in one day. I will only be given two grams of starting material so I am thinking of using .5 grams of salicylaldehyde and .5 grams of aniline just incase I mess up. So I need to know how much HoAc and EtoH I would need to make the imine in the first step? How exactly would I calculate the amount of reagents I need for this synthesis? Should I wait until the next week to do the second reaction step or can this be done in one day?
NH 2. OH f-Explanation / Answer
Imine formation is usually done in alcohols so whatever your TA suggested is good. If you use dichloromethane insteat you can use anhydrous sodium sulfate to scavenge the water molecules which will be forming during the course of the reaction. Using acetic acid is also a good choice this will increase the reactivity of aniline (since the electron pair on N atom will involve in resonance aniline will be less reactive, addition of acid will disturb this resonance and make the compound reactive). So you can go ahead with your TA suggestion but remember minimum 2 hours of stirring is need for the completion, even you can reflux the reaction mixture. Acetic acid amount will be catalytic lets say 10-20 mol% is sufficient do not add much because removal of AcOH under vaccum is difficult.