Acetone → 2,4,6-Trimethyl-2,3-dihydro-1H-inden-1-ol

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Reaction Steps

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.

Provenance & Evidence