HCID 53714028, compound → Cyclopentaneacetic acid, 3-oxo-2-propyl-, methyl ester

Temperature

40 °C

Into a 1 liter flask purged with dry nitrogen, there is introduced 210 ml of anhydrous methanol followed by 63.2 g of aluminium triisobutyl over thirty minutes. The resulting solution is refluxed for one hour. After cooling, the solution is introduced into an autoclave with 6.5 g of 5.3% palladium on carbon. 58.8 g (0.30 mole) of methyl[2-n-propyl-3-keto-cyclopent-1-en-1-yl]-acetate is added. The autoclave is closed, shaken to homogenise the mass and heated to 40°C. Hydrogen is then introduced under a pressure of 10 kg/cm2 until no further hydrogen absorption occurs. After cooling, the mass is filtered to separate the catalyst, poured into water and extracted with petroleum ether (3 × 100 ml). The petroleum ether solution is washed to neutrality and distilled. 53 g of crude product are thus obtained which are rectified under reduced pressure. 43.8 g of methyl [2-n-propyl-3-keto-cyclopent-1-yl]-acetate is thus obtained, presenting the following characteristics:

1. customInto a 1 liter flask purged with dry nitrogen, there
2. additionis introduced 210 ml of anhydrous methanol
3. waitfollowed by 63.2 g of aluminium triisobutyl over thirty minutes
4. temperatureThe resulting solution is refluxed for one hour
5. temperatureAfter cooling
6. additionthe solution is introduced into an autoclave with 6.5 g of 5.3% palladium on carbon
7. customThe autoclave is closed
8. stirringto homogenise the mass
9. temperatureAfter cooling
10. filtrationthe mass is filtered
11. customto separate the catalyst
12. additionpoured into water
13. extractionextracted with petroleum ether (3 × 100 ml)
14. washThe petroleum ether solution is washed to neutrality
15. distillationdistilled
16. custom53 g of crude product are thus obtained which

ORD record

ord-76c865bd653c469fbb484d00b30ce12d

Source dataset

uspto-grants-1976_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03970682