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

HRID 328847Notes

Reaction equation

HRID 328847 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+]>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

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 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 1

HCID 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° centigrade as 47.0 ml. of 12N aqueous H 2 SO 4 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 H 2 O. 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° centigrade as 47.0 ml
  4. additionof 12N aqueous H 2 SO 4 was added over 1.25 hours as the internal temp
  5. temperaturewas maintained at 20° centigrade
  6. additionin addition to traces of starting material
  7. washThe ether solutions were washed with water and brine
  8. dry with materialdried over NaSO4

Sources & evidence

ORD record
ord-aa1a3b04132f49799b6f9496c01a9aa8
Source dataset
uspto-grants-1977_04
Patent number
US04018799

Reaction notes

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