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

HRID 268411노트

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HRID 268411 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

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온도
15 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-7102941752f74cbe88e88faa0bf131a9
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03947473

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