Isopropanol → HCID 19049283, compound

The previously obtained 63.0 g of 1-(4'benzyloxy-3'-methoxyphenyl)-4-methylpentanol was dissolved in 310 ml of acetone. To this mixture, Jones reagent was added dropwise at 0° to 10° C. while cooling in an ice bath. After the completion of dropping, 50 ml of isopropyl alcohol was added to the solution and the resultant mixture was stirred at room temperature until the solution turned to green. Subsequently, the reaction solution was extracted with 400 ml of dichloromethane three times. The extraction solution obtained was washed with 300 ml of water, 300 ml of saturated aqueous sodium hydrogen carbonate solution, and 300 ml of brine, in this order. After dried over anhydrous magnesium sulfate, the solution was concentrated under reduced pressure, affording a brown crystal. The crystal were recrystallized from ether-hexane, affording 51.6 g of 4'-benzyloxy-3'-methoxy-4-methylvalerophenone (82.6% yield).

1. temperaturewhile cooling in an ice bath
2. extractionSubsequently, the reaction solution was extracted with 400 ml of dichloromethane three times
3. customThe extraction solution obtained
4. washwas washed with 300 ml of water, 300 ml of saturated aqueous sodium hydrogen carbonate solution, and 300 ml of brine, in this order
5. dry with materialAfter dried over anhydrous magnesium sulfate
6. concentrationthe solution was concentrated under reduced pressure
7. customaffording a brown crystal
8. customThe crystal were recrystallized from ether-hexane

ORD record

ord-f413955ddbbd4f339f3a7af6e5730fbe

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05629340