4-cyclopentylpentanoic acid → HCID 22476837, compound

A solution of 4-cyclopentylpentanoic acid (16 g; 94 mmol) in diethyl ether (30 ml) and THF (30 ml) was added within 20 minutes to lithium aluminum hydride (3.6 g; 94 mmol) and suspended in the same solvent (100 ml). After 2 hours at reflux, the reaction mixture was cooled with an ice-bath and quenched successively with water (4 ml), 15% sodium hydroxide (12 ml) and again water (4 ml). The white solid was filtered off, and the mixture diluted with MTBE (300 ml), washed with 1 N HCl (300 ml), sodium bicarbonate solution (300 ml) and brine (2×300 ml), dried (MgSO4), concentrated in vacuo, and distilled (59° C./0.075 torr) to give 8.7 g (59% yield) of 4-cyclopentylpentan-1-ol.

1. temperatureAfter 2 hours at reflux
2. temperaturethe reaction mixture was cooled with an ice-bath
3. customquenched successively with water (4 ml), 15% sodium hydroxide (12 ml) and again water (4 ml)
4. filtrationThe white solid was filtered off
5. additionthe mixture diluted with MTBE (300 ml)
6. washwashed with 1 N HCl (300 ml), sodium bicarbonate solution (300 ml) and brine (2×300 ml)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo
9. distillationdistilled (59° C./0.075 torr)

ORD record

ord-193520f874c949cdb0cda4862da6cd1a

Source dataset

uspto-grants-2002_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06441052B1