Hydrochloric Acid → HCID 19855884, compound

To a solution of 8-oxo-9-decenoic acid (910 mg, 4.94 mmol, 1.00 eq.) in MeOH (20.0 mL), was added CeCl3.7H2O (2.76 g, 7.41 mmol, 1.50 eq.). The mixture was stirred for 30 minutes with ice-cooling, and then thereto was slowly added sodium borohydride (224 mg, 5.93 mmol, 1.20 eq.). The mixture was stirred for 1 hour, and then the reaction solution was poured into 1 M aqueous hydrochloric acid solution. The organic phase was extracted with chloroform. Then, the resulting organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=97:3) to obtain 8-hydroxy-9-decenoic acid as shown below (870 mg, 4.55 mmol, 92%).

1. temperaturecooling
2. stirringThe mixture was stirred for 1 hour
3. extractionThe organic phase was extracted with chloroform
4. dry with materialThen, the resulting organic phase was dried over magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (elution solvent: chloroform/methanol=97:3)

ORD record

ord-d0b388f9307c47cead958e456c66d9f1

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073802B2