Synthesis and Analysis of Organic and Inorganic Compounds (CM3102)

2017 Spring semester

Week 7: Multi-step Synthesis (ROMP project-2)

Objective:
1. To continue multi-step synthesis toward the ROMP monomer.
2. To practice intermediate treatment and purification.

Apparatus:
magnetic stirrer / diaphragm pump / Buchner funnels (2) / 20 mL vials (3) / 100 mL round bottom flask
/ 11.5 egg-shaped stir bar / rubber septum (2) / 50 mL graduated cylinder / 3 mL and 10 mL
syringes with disposable needles / 1000 mL suction flask with rubber gasket / 5 mm NMR tubes (2)
/ squeeze bottles (2) for ACN and diethyl ether

Briefly summarized synthetic procedure

Continue from week 6

1. Observe crystal formation and shape of the crystal. Filter the crystals formed in the reaction mixture
and wash with diethyl ether.
2. Dry the product in a vacuum oven (skip)

Synthesis of N-phenyl-exo-7-oxanorbornene-amic acid (2)

1. In a round bottom flask, dissolve compound 1 (3 g, 18.06 mmol) in 25 mL of acetonitrile (ACN)
2. Dissolve 1.65 mL of aniline in 5 mL of ACN. Add the aniline solution to the round bottom flask and
stir the reaction mixture for 1 h at room temperature. NMR sampling for compound 1 (CDCl3).
3. Collect the precipitate (formed in the reaction mixture) by filtration and wash with ACN (finally
diethyl ether).
4. Dry the product (vial and EP tube for NMR) in an oven.

=> move on to next week

O O Grubb's O
O H 2N O O H O O
AcONa catalyst n
O + O O N N
THF ACN COOH Ac2O O O
O O N
O
1 2 3
-
exo-7-oxanorbornene exo-N-phenyl- exo N-phenyl-7-oxanorbornene
dicarboxlic anhydride 7-oxanorbornene amic acid dicarboximide
4
poly(exo-N-phenyl-7-
oxanorbornene
dicarboximide)

Safety Considerations

Most of the chemicals used in this experiment are harmful to inhale, ingest, or contact and many are
flammable; therefore, students must be extremely careful all through the experiment. Particularly,
diethyl ether is extremely volatile and flammable. Always work in the fume hood with the sash pulled
down as low as possible. Gloves, eye protections, and lab coats must be worn at all times in the
laboratory.
 Synthesis and Analysis of Organic and Inorganic Compounds (CM3102)
2017 Spring semester

Before you come to the lab

1. Be aware of the chemical structures and usage of reagents in this experiment.

2. Be aware of the safety considerations of all the chemicals used in the experiment. You can obtain
important information from MSDS (material safety data sheet). For example, google furan MSDS and
you can find safety information about furan.

3. You should review and understand the carboxylic anhydride ring opening reaction mechanism.

4. You should predict 1H NMR peaks from compound 1 and 2. Both chemical shifts and splitting
patterns.

Pre-Lab Question

1. Before you come to the lab, find out commonly used organic solvents. I suggest you to make a
table of organic solvents with their abbreviations and properties (e.g., bp, polarity, protic/aprotic,
solubility).

2. In this reaction, we use acetonitrile as a solvent. Is there any specific reason for using acetonitrile?
Both acetonitrile and methanol are commonly used polar organic solvents. Why we did not choose
methanol in this reaction?