I will be performing a synthesis in lab using this scheme except p-TsOH and CH2C

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?

Explanation / Answer

imine can be formed using acetic acid in catalytic amount and absolute ethanol as solvent

1) Salicylaldehyde ( 500mg, 4.1mmol) and aniline ( 381mg, 4.1mmol) in absolute ethanol (5ml, 10V) was added 1drop of acetic acid (cat.) The overall reaction mixture was refluxed for (1-4) hours ,the reaction was monitored by TLC until the disappearance of starting materials.

imine formed can be reduced insitu using NaBH4 ( 187mg, 4.92mmol, 1.2 eq.) you may be able to complete both steps in one day using above protocol

Related Questions

Navigate

• Browse (All)
• Browse I
• Subjects