Hydrochloric Acid → 3-Phenylprop-2-Enal

HRID 981175Notes

Reaction equation

HRID 981175 reaction equation
[C:1](#N)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl.[OH-:22].[Al+3].[OH-].[OH-]>O1CCCC1.C1(C)C=CC=CC=1>[CH:1](=[O:22])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 746673-Phenylprop-2-enenitrileHCID 10176082Aluminum HydroxideHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 3073-Phenylprop-2-EnalYield 63.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8 g cinnamonitrile in 100 ml tetrahydrofuran, was added dropwise 50 ml of a 1.5M toluene solution of diisobutylaluminum hydride with ice cooling, and the resulting mixture was stirred at room temperature for two hours. The reaction mixture was slowly poured to 200 ml ice water, hydrochloric acid was then added to dissolve the aluminum hydroxide formed, and the organic layer was collected and dried. Distillation of the dried solution under reduced pressure gave 5.2 g (yield: 63.6%) of cinnamaldehyde.

Workup

  1. additionwas then added
  2. customformed
  3. customthe organic layer was collected
  4. customdried
  5. distillationDistillation of the dried solution under reduced pressure

Sources & evidence

ORD record
ord-96932cc78d7d4b41b66c428e8b288de9
Source dataset
uspto-grants-1991_02
Patent number
US04990529

Reaction notes

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