3-Phenylprop-2-Enal → HCID 54098440, compound

HRID 1709626Notes

Reaction equation

HRID 1709626 reaction equation
[CH:1](=O)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH:12]([CH2:18][CH2:19][CH2:20][CH3:21])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1(C)C=CC=CC=1.[Zn]>[CH2:18]([C:12](=[CH:1][CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 3073-Phenylprop-2-EnalHCID 79072Ethyl 2-bromohexanoate

Product 1

HCID 54098440HCID 54098440, compoundYield 38.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent2×

Procedure

In a 500 ml three necked flask was placed 7.0 g Zn dust and 0.7 g Cu powder in 150 ml dry toluene. To this suspension was added a solution of 13.2 g (0.1 mol) cinnamaldehyde and 22.3 g (0.1 mol) ethyl 2-bromohexanoate in 100 ml toluene. The reaction was refluxed overnight under nitrogen, cooled to room temperature and washed two times with 140 ml of 20% acetic acid and two times with 150 ml water. The organic phase was dried over magnesium sulfate and the solvent removed by rotary evaporation. Distillation of the crude product (24.9 g) resulted in isolation of 10.0 g ethyl 2-butyl-5-phenyl-pentadienoate. BP: 135-138 @ 0.1 mm Hg UV (CH2C12): λmax 315, ε=33,280, K=129.

Workup

  1. temperatureThe reaction was refluxed overnight under nitrogen
  2. washwashed two times with 140 ml of 20% acetic acid and two times with 150 ml water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent removed by rotary evaporation
  5. distillationDistillation of the crude product (24.9 g)

Sources & evidence

ORD record
ord-c35159bb5bb04915a4f63b70b2c53572
Source dataset
uspto-grants-1990_08
Patent number
US04950467

Reaction notes

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