Benzaldehyde → 3-Phenylprop-2-enenitrile

HRID 981174Notes

Reaction equation

HRID 981174 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 69%

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-cc01535135c049208ad1cfa870fee79b
Source dataset
uspto-grants-1991_02
Patent number
US04990529

Reaction notes

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