[C:1]([O:4][C:5]1[C:6]([CH3:19])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([OH:18])([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].CS(C)=O.[C-:24]#[N:25].[K+].OS(O)(=O)=O>O.C(OCC)C>[C:24]([C:10]([OH:18])([CH2:9][CH2:8][C:7]1[C:6]([CH3:19])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[C:14]([CH3:15])=[C:13]([CH3:16])[C:12]=1[OH:11])[CH3:17])#[N:25]A solution of 2.4 g. (0.1 mol.) of rac. 6-acetoxy-2-hydroxy-2.5,7,8-tetramethylchroman in a total of 200 ml. of dimethyl-sulfoxide was rapidly stirred as 32.5 g. (0.5 mol.) of granular KCN was added thereto by sifting so that a uniformly dispersed suspension was obtained. The resulting suspension was cooled to 15° centigrade as 47.0 ml of 12N aqueous H2SO4 was added over 1.25 hrs. as the internal temp. was maintained at 20 degrees centigrade. Tlc at this point showed a major, slowerrunning spot in addition to trace of starting material. The material was poured into diethylether and H2O. The ether soulutions were washed with water and brine, dried over NaSO4 and stripped of solvent to yield rac. 2-cyano-4-(5-acetoxy-2-hydroxy-3,4,6,-trimethylphenyl)-butan-2-ol as a gum.
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