Reaktion #2512487

Reaktionsgleichung

water

NaBH4

2,4,6-trimethyl-indan-1-one

acetone

→

yellow sticky solid

Ausbeute 93.9%

2,4,6-trimethylindan-1-ol

Ausbeute 93.9%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a magnetic stirring bar
2. 2
   Sonstigethe temperature below 20° C.
3. 3
   workup.ADDITIONduring the addition
4. 4
   Sonstige(careful: exothermic reaction!)
5. 5
   Sonstigesubsequently the solvents removed
6. 6
   Sonstigegiving a white solid
7. 7
   Extraktionextracted with toluene (2×150 mL)
8. 8
   ExtraktionThe water phase was further extracted with toluene
9. 9
   Waschenwashed with a 10% aqueous solution of NH4Cl
10. 10
    WaschenAfter washing
11. 11
    Trocknenthe organic phase was dried over Na2SO4
12. 12
    Filtrationfiltered
13. 13
    Sonstigeevaporated

Vorschrift

37.48 g of 2,4,6-trimethyl-indan-1-one (0.215 mol) were dissolved in 200 mL of EtOH in a 500 mL, 3-neck rounded bottom flask equipped with a magnetic stirring bar, a thermometer and a reflux condenser. NaBH4 (15.01 g, 0.397 mol) was then slowly added keeping the temperature below 20° C. during the addition. The light yellow suspension was stirred at r.t. for 18 h. Then 100 mL of acetone were cautiously added (careful: exothermic reaction!) and subsequently the solvents removed giving a white solid. The latter was treated with 100 mL of water and extracted with toluene (2×150 mL). The water phase was further extracted with toluene, the organic phases were combined and washed with a 10% aqueous solution of NH4Cl. After washing, the organic phase was dried over Na2SO4, filtered and evaporated to give 35.57 g of a yellow sticky solid: its 1H-NMR analysis showed the target product as 1.4/1 mixture of two diastereoisomers, contaminated by 5% wt. of starting indanone (yield 89.2%). The product was used as such in the next step without further purification.

Quelle