Sodium Cyanide → 5,5-Diphenylvaleronitrile

HRID 565652Notes

Reaction equation

HRID 565652 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)=O.[C-:22]#[N:23].[Na+]>CS(C)=O>[C:10]1([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:8][CH2:7][CH2:6][C:22]#[N:23])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 138807014,4-Diphenylbutyl methanesulfonate

Product 1

HCID 137771625,5-DiphenylvaleronitrileYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4,4-diphenylbutyl methanesulfonate (7.5 g) and sodium cyanide (2.5 g) in dimethyl sulfoxide (70 mL) was stirred at 60° C. for 15 hours. After the reaction mixture was allowed to cool, it was extracted with diethyl ether. The extract was dried over MgSO4 and concentrated, whereby 5.8 g of the title compound was obtained quantitatively.

Workup

  1. temperatureto cool
  2. extractionit was extracted with diethyl ether
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-df207343961c443d8f00aa7da616407b
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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