Acetone → HCID 10330105, Verbindung

Reaktionsgleichung

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12](=[O:14])[CH3:13])=[CH:9][CH:8]=[CH:7]2.[BH4-].[Na+].CC(C)=O>C(O)C>[OH:14][CH:12]([C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([OH:1])=[CH:3][CH:4]=[CH:5]2)[CH3:13]

Komponenten

Versuchsvorschrift

1040 g of 8'-hydroxy-1'-acetonaphthone was dissolved in 8.5 liters of ethanol, to which 131 g of sodium borohydride was added while ice-cooling in order not to allow the temperature of the reaction solution to exceed 30° C. After agitation for 30 minutes at room temperature, excess sodium borohydride was decomposed with 1 liter of acetone. The reaction solution was concentrated under reduced pressure, after which 4 liters of 1N hydrochloric acid was added, followed by extraction with ethyl acetate. The resultant organic phase was washed with a saturated saline solution to remove the excess acid. After drying with anhydrous magnesium sulfate, the solvent was distilled off and a small amount of hexane was added to the resultant residue for crystallization. The crystals were collected by filtration to obtain 1000 g of the captioned compound as light brown crystals.