Hexane → HCID 57686811, compound

HRID 251817Notes

Reaction equation

HRID 251817 reaction equation
C[Al](C)C.[CH3:5]CCCCC.CNCCNC.[C:17]([C:19]1[CH:20]=[C:21]([CH:26]=[C:27]([O:29][CH2:30][CH2:31][O:32][CH3:33])[CH:28]=1)[C:22]([O:24]C)=O)#[N:18]>C1(C)C=CC=CC=1.O>[C:22]([C:21]1[CH:20]=[C:19]([CH:28]=[C:27]([O:29][CH2:30][CH2:31][O:32][CH3:33])[CH:26]=1)[C:17]#[N:18])(=[O:24])[CH3:5]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8070N,N'-DimethylethylenediamineHCID 16682925TrimethylaluminumHCID 21942473Benzoic acid, 3-cyano-5-(2-methoxyethoxy)-, methyl ester

Product 1

HCID 57686811HCID 57686811, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Solution of AlMe3 in hexane (19 mmol) was dropped to the solution of DMEDA (24 mmol) in 60 ml dry toluene slowly at 0° C. under N2. The solution was then continued to stir at room temperature for another 1 h and added methyl 3-cyano-5-(2-methoxyethoxy)benzoate (17.3 mmol) and stirred at reflux for 8 h. The mixture was poured to the water and extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered, and concentrated to give 3-acetyl-5-(2-methoxyethoxy)benzonitrile (58.6%).

Workup

  1. stirringstirred
  2. temperatureat reflux for 8 h
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82ea3c6a260e4529832829e7c668d42b
Source dataset
uspto-grants-2011_01
Patent number
US07868001B2

Reaction notes

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