Benzaldehyde → 3-Phenylprop-2-enenitrile

HRID 1904683Notes

Reaction equation

HRID 1904683 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(OCC)=O)C.[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>O1CCCC1>[C:12](#[N:13])[CH:11]=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 746673-Phenylprop-2-enenitrileYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Four grams of 60% sodium hydride was suspended in 100 ml tetrahydrofuran, and 17.1 g of diethylphosphonoacetonitrile was added with ice cooling. To the resulting solution, was added dropwise a solution of 10.6 g benzaldehyde in 80 ml tetrahydrofuran, and the mixture was stirred for one hour. After admixing 50 ml water, the organic layer was collected, dried over anhydrous sodium sulfate and concentrated. Distillation of the concentrate under reduced pressure (102°-106° C./6 mmHg) gave 8.9 g (yield: 69.0%) of cinnamonitrile.

Workup

  1. customthe organic layer was collected
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. distillationDistillation of the
  5. concentrationconcentrate under reduced pressure (102°-106° C./6 mmHg)

Sources & evidence

ORD record
ord-48329806f4dd4281b28f26609a403720
Source dataset
uspto-grants-1989_06
Patent number
US04839376

Reaction notes

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