[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][C:14](=[O:16])[CH3:15])=[C:7]([CH3:17])[C:6]=1[CH2:18][CH2:19][C:20](=[O:22])[CH3:21])(=[O:3])[CH3:2].C[N:24]([CH3:27])C=O.[C-]#N.[K+].OS(O)(=O)=O>O>[C:27]([C:20]([OH:22])([CH2:19][CH2:18][C:6]1[C:7]([CH3:17])=[C:8]([O:13][C:14](=[O:16])[CH3:15])[C:9]([CH3:12])=[C:10]([CH3:11])[C:5]=1[O:4][C:1](=[O:3])[CH3:2])[CH3:21])#[N:24]A solution of the crude 4-(2,5-diacetoxy-3,4,6-trimethylphenyl) butan-2-one prepared in Example 56 in 963 ml. of dimethylformamide was cooled under N2 in an ice bath. A solution of 69.4 g. of potassium cyanide in 150 ml. of H2O was added over 20 minutes. The mixture was stirred another 10 minutes and then 161 ml. of 6N H2SO4 was added dropwise over 20 minutes while an internal temperature of +10° to +13° was maintained. The viscous suspension (pH 8) was stirred another 30 minutes, brought to pH 4 by the addition of 16.5 ml. of 6N H2SO4, poured into ice-H2O, and extracted with ether. The ether solutions were washed with brine, dried over Na2SO4, and stripped of solvent to give (±)-2-cyano-4-(2,5-diacetoxy-3,4,6-trimethylphenyl)butan-2-ol as an orange-brown foam.
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