Hydrochloric Acid → 4-Hydroxy-4-(4-(4-pentylcyclohexyl) cyclohexyl)butanal propylene acetal

To Grignard reagent prepared from 33.7 g (173 mmol) of 2-(2-bromoethyl)-1,3-dioxane and magnesium in 300 ml of tetrahydrofuran (THF), a solution of 40.0 g (151 mmol) of 4-(4-pentylcyclohexyl) cyclohexane carbaldehyde (10) in 200 ml of THF was added dropwise, and the resultant solution was stirred for 3 hours. The reaction solution was added into 500 ml of 1N-hydrochloric acid, and the reaction product was extracted with 300 ml of toluene. The formed organic layer was sequentially washed with a saturated aqueous solution of hydrogen sodium carbonate and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane) to obtain 47.5 g (125 mmol) of 4-hydroxy-4-(4-(4-pentylcyclohexyl) cyclohexyl)butanal propylene acetal (11) at a yield of 82.8 percent.

1. extractionthe reaction product was extracted with 300 ml of toluene
2. washThe formed organic layer was sequentially washed with a saturated aqueous solution of hydrogen sodium carbonate and water
3. dry with materialdried over anhydrous magnesium sulfate
4. distillationThe solvent was distilled off under reduced pressure
5. customthe residue was purified by silica gel column chromatography (eluent: hexane)

ORD-Eintrag

ord-144a5ca3c7074b02a418fd61661a630b

Quelldatensatz

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06146718