Butyric Acid → 5-Norbornene-2-carboxylic acid

and 25 ml of toluene were continuously added to the 250 ml flask. Zirconium acetyl acetonate [Zr(acac)4] (0.658 g, 0.135 mmol, 1 mol %) was added thereto, and azeotropic reflux was performed. The temperature of the heated bath was controlled to 150° C. and the reaction was performed for 18 hours. After that, the reaction was finished after the GC check, and it was cooled to normal temperature. Thereafter, 30 mlm of ethyl acetic acid was added thereto. After the undissolved solid compound is precipitated, 30 ml of 1 M (mol/L) dilute hydrochloric acid solution was added thereto, and the washing was performed. This process was performed twice, and 30 ml of the saturated aq.NaHCO3 solution was added thereto and washed. This process was performed twice, and MgSO4 was added to the separated organic solution to remove a small amount of water. After water was removed, this was filtered by using MgSO4, and the solvent was removed under reduced pressure. The purification process was carried out to obtain 4.15 g of the compound (molecular weight=342.15, yield 89%).

1. temperatureazeotropic reflux
2. customwas controlled to 150° C.
3. temperaturewas cooled to normal temperature
4. customAfter the undissolved solid compound is precipitated
5. addition30 ml of 1 M (mol/L) dilute hydrochloric acid solution was added
6. additionNaHCO3 solution was added
7. washwashed
8. additionMgSO4 was added to the separated organic solution
9. customto remove a small amount of water
10. customAfter water was removed
11. filtrationthis was filtered
12. customthe solvent was removed under reduced pressure

ORD record

ord-9622d8cd6f2642f9a97a883a1e6d5b2e

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563764B2