Dimethyl Sulfoxide → Rac. 2-cyano-4-(5-acetoxy-2-hydroxy-3,4,6,-trimethylphenyl)-butan-2-ol

HRID 268411Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 15 °C

Procedure

A solution of 26.4 g. (0.1 mol.) of (±)-6-acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman in 200 ml. of dimethylsulfoxide was rapidly stirred as 32.5 g. (0.5 mol.) of granular KCN was added by sifting so that a uniformly dispersed suspension was obtained. The resulting mixture was cooled to 15°C. as 47.0 ml. of 12N aqueous H2SO4 was added over 1.25 hours as the internal temp. was maintained at 20°C. Tlc at this point showed a major, slower-running spot in addition to traces of starting material. The material was poured into diethylether and H2O. The ether solutions were washed with water and brine, dried over NaSO4 and stripped of solvent to yield (±)-2-cyano-4-(5-acetoxy-2-hydroxy-3,4,6-trimethylphenyl)butan-2-ol as a gum.

Workup

filtrationby sifting so that a uniformly dispersed suspension
customwas obtained
temperaturewas maintained at 20°C
additionin addition to traces of starting material
washThe ether solutions were washed with water and brine
dry with materialdried over NaSO4

Sources & evidence

ORD record: ord-7102941752f74cbe88e88faa0bf131a9
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03947473

Reaction notes

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