Phenylacetonitrile → HCID 73110302, compound

HRID 513977Notes

Reaction equation

HRID 513977 reaction equation
[Na].[CH2:2]([C:9]#[N:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:11][C:12]([CH3:16])=[CH:13][CH:14]=O>CO>[CH3:11][C:12]([CH3:16])=[CH:13][CH:14]=[C:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:9]#[N:10]

Participants

5

Reactant 3

HCID 8794PhenylacetonitrileHCID 610203-Methyl-2-butenalHCID 5360545Sodium

Product 1

HCID 73110302HCID 73110302, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium (9.2 g, 0.4 mol) is dissolved in methanol (130 ml) and benzylcyanide (46.8 g, 0.40 mol) is added, followed by the careful addition of a solution of 3-methyl-2-butenal (40.3 g, 0.48) in methanol (100 ml). The resulting suspension is stirred for 20 h at room temperature and then worked up following the procedure described in Example 2. The crude product is crystallized twice from hexane to yield 5-methyl-2-phenyl-hexa-2,4-diene nitrile (44.9 g, 61%), m.p. 66-67° C.

Workup

  1. customThe crude product is crystallized twice from hexane

Sources & evidence

ORD record
ord-3cbc83a649cb4d96844cc98447de9893
Source dataset
uspto-grants-2015_08
Patent number
US09102899B2

Reaction notes

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