Experiment 10. Preparation of 3-Phenylthousobenzofuran-1- one from 3-Hydroxyisob

Question

Experiment 10. Preparation of 3-Phenylthousobenzofuran-1- one from 3-Hydroxyisobenzofuran-1-one Introduction (10-1) Procedure with 1 0 g of phthaldehydic acid (2 at oxybenaaldehyde), 30 mL of benene,75 mL of benzenethiol and a crystal of toluenesulfonic acid. Place a Dean-Stack srap filled with benzene and fited with a condenser and drying tube, on top of the flask Spot TLC of the reaction misture Reflux the mixture for 75 minutes to remove water, visually monitoring any changes. Cool the raction mixture and perform TLC to insure that the reaction is complete Transfer the solutioe to a separatory funnel using ethyl acetate. Remove the Rethax themixturefor 75mintestogtteontopoftbeflask Spot TLC ofthe eaction benene TLC to insure that the reaction is complete. Transfer the solution aqueous phase and wash the with two 20 mL portions of I M sodium hydroxide solution. This should be followed b shings with 50 mL of water and then with 25 mL of brine. Dry the organic phase with sodiu Ifate and filter it. Place the solution into a pre-weighed round-botom flask and evaporate t ent using a rotary evaporator. Reweigh the flask containing the prodact and determine t ld. Questions Propose the mechanism for the reaction given in scheme 10-1. 2 Why is the organic phase washed with NaOH, but not with NaHICO, or HCT

Explanation / Answer

In the preparation of 3-phenyl thioisobenzofuran-1-one, the organic phase is washed with NaOH, but not with NaHCO3 or HCl. If we use NaHCO3 or HCl, to wash the organic phase salt can be formed. So that we use NaOH.

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