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

HRID 1415230Notes

Reaction equation

HRID 1415230 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

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 144156666-Acetoxy-2-hydroxy-2,5,7,8-tetramethylchroman

Product 1

HCID 21432304Rac. 2-cyano-4-(5-acetoxy-2-hydroxy-3,4,6,-trimethylphenyl)-butan-2-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

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 degrees centigrade as 47.0 ml. of 12N aqueous H2SO4 was added over 1.25 hours as the internal temp. was maintained at 20° centigrade. 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

  1. filtrationby sifting so that a uniformly dispersed suspension
  2. customwas obtained
  3. temperatureThe resulting mixture was cooled to 15 degrees centigrade as 47.0 ml
  4. temperaturewas maintained at 20° centigrade
  5. additionin addition to traces of starting material
  6. washThe ether solutions were washed with water and brine
  7. dry with materialdried over NaSO4

Sources & evidence

ORD record
ord-f71c60466ec84b29a25e5a7630a538df
Source dataset
uspto-grants-1977_01
Patent number
US04003919

Reaction notes

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