C([O-])(C)(C)C.[K+].[C:7](#[N:9])[CH3:8].[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH:14]=[O:15]>C1COCC1>[OH:15][CH:14]([C:13]1[CH:16]=[CH:17][CH:18]=[C:11]([OH:10])[CH:12]=1)[CH2:8][C:7]#[N:9]To a stirred suspension of t-BuO−K+ (68.5 g, 614 mmol) in THF, cooled to −50° C., was added acetonitrile (30.3 mL, 540 mmol), dropwise over a period of 5 min. The resulting mixture was stirred at −50° C. for 30 min following which a solution of 3-hydroxybenzaldehyde (21.2) (30.0 g, 244 mmol) in THF was added slowly, over a period of 10 min. This was then allowed to warm to 0° C. and stirred for another 3 h during which the reaction was complete. The reaction was quenched by slow addition of ice-water followed by extraction with EtOAc. The combined organics were washed with water, brine and dried over Na2SO4. The solution was concentrated under reduced pressure to give 3-hydroxy-3-(3-hydroxyphenyl)propanenitrile (21.16) as yellow oil which was purified by flash column chromatography (0 to 20% EtOAc—hexanes gradient). Yield (25.0 g, 62%); 1H NMR (400 MHz, CDCl3) δ 7.27 (s, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.90-6.93 (m, 1H), 6.82 (dd, J=8.0, 2.4 Hz, 1H), 4.91-5.03 (m, 1H), 2.76 (d, J=6.4 Hz, 2H).
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