Acetone → HCID 519595, compound
Reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH3:12][C:13]([CH3:15])=O>CO>[CH3:12][C:13]([CH3:15])=[C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]#[N:9]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
Benzyl cyanide (50.0 g, 0.43 mol) is dissolved in a mixture of acetone (150 ml) and methanol (20 ml) and then KOH (10 g, 0.15 mol) is added under stirring. After complete dissolution the brown mixture is heated to 65° C. (oil bath) during 90 min. The mixture is concentrated in a rotary evaporator, the residue is dissolved in toluene and washed 3 times with half saturated aq. NaCl-solution. The organic layer is dried over MgSO4, the solvent removed under reduced pressure and the residue distilled over a short-path apparatus at 0.07 mbar. The fraction distilling at 77° C. is collected (33 g) and subjected to a fine distillation over a Widmer-column to yield 31.3 g (47%) of 3-methyl-2-phenyl-but-2-ene nitrile as colourless oil (b.p. 85° C./0.05 mbar).
Workup
- dissolutionAfter complete dissolution the brown mixture
- concentrationThe mixture is concentrated in a rotary evaporator
- dissolutionthe residue is dissolved in toluene
- washwashed 3 times with half saturated aq. NaCl-solution
- dry with materialThe organic layer is dried over MgSO4
- customthe solvent removed under reduced pressure
- distillationthe residue distilled over a short-path apparatus at 0.07 mbar
- distillationThe fraction distilling at 77° C.
- customis collected (33 g)
- distillationsubjected to a fine distillation over a Widmer-column
Sources & evidence
- ORD record
- ord-5a398e3f6b2e4adca86ec4d65deb68e1
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102899B2
Reaction notes
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