Hexanal → HCID 67526844, compound

HRID 513973Notes

Reaction equation

HRID 513973 reaction equation
[Na].[CH2:2]([C:9]#[N:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>CO>[C:3]1([C:2](=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:9]#[N:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6184HexanalHCID 8794PhenylacetonitrileHCID 5360545Sodium

Product 1

HCID 67526844HCID 67526844, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium (27.6 g, 1.2 mol) is dissolved in methanol (550 ml) and benzyl cyanide (140.4 g, 1.2 mol) is added, followed by dropwise addition over 45 min. of hexanal (164.2 g, 1.44 mol), keeping the inside temperature between 20-25° C. The mixture is further stirred during 90 min. at room temperature, and then extracted 3 times with hexane. The organic layers are washed with water, 2 N aq. HCl-solution, then brine. The organic layer is dried over MgSO4, the solvent removed under reduced pressure and the residue distilled over a short-path apparatus at 0.04 mbar. The fraction distilling at 114-121° C. is collected (172 g) and subjected to a fine distillation over a Widmer-column to yield olfactorily pure 2-phenyl-oct-2-ene nitrile (113 g, 44%) as a colourless oil (b.p. 113-115° C./0.03 mbar).

Workup

  1. custombetween 20-25° C
  2. extractionextracted 3 times with hexane
  3. washThe organic layers are washed with water, 2 N aq. HCl-solution
  4. dry with materialThe organic layer is dried over MgSO4
  5. customthe solvent removed under reduced pressure
  6. distillationthe residue distilled over a short-path apparatus at 0.04 mbar
  7. distillationThe fraction distilling at 114-121° C.
  8. customis collected (172 g)
  9. distillationsubjected to a fine distillation over a Widmer-column

Sources & evidence

ORD record
ord-010a543baea84448b772c18fe5387747
Source dataset
uspto-grants-2015_08
Patent number
US09102899B2

Reaction notes

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