[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C:11]2=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[OH:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]A 3 L one neck flask fit with an overhead stirrer, condenser, nitrogen inlet, solids addition funnel, and thermometer was charged with crude 6-t-butyl-1-indanone (109 g, 0.577 mol) and anhydrous ethanol (1.5 L). The reaction was heated to 30-40° C. and sodium borohydride (43.6 g, 1.15 mol) was added over the course of 30 min followed by heating to reflux overnight. The next day an additional amount of sodium borohydride is added (12.0 g, 0.32 mol) and reflux continued for an hour. The reaction was cooled, quenched in 5% HCl/ice (1 L), extracted into diethyl ether (1 L), and the organic layer washed with water (14×150 mL), and dried over anhydrous sodium sulfate. Rotary evaporation to remove the solvent gave crude 6-t-butyl-1-indanol (64.4 g). Another diethyl ether extraction as above gave an additional amount of crude 6-t-butyl-1-indanol (75.5 g total). 1HNMR (CDCl3, 500 MHz) δ7.46 (s, 1H); 7.32 (dd, JAB=1.5, 8 Hz, 1H); 7.19 (d, JAB=8 Hz, 1H); 5.24 (t, J=6 Hz); 3.01 (m, 1H); 2.78 (p, J=7.5 Hz, 1H); 2.50 (m, 1H); 1.95 (m, 1H); 1.32 (s, 9H).
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