Potassium Carbonate → (E)-4-butoxy-3-methoxycinnamic acid methyl ester

HRID 2307521Notes

Reaction equation

HRID 2307521 reaction equation
[CH3:1][O:2][C:3](=[O:15])/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:11]([OH:12])=[C:8]([O:9][CH3:10])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:1][O:2][C:3](=[O:15])/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:11]([O:12][CH2:3][CH2:4][CH2:5][CH3:6])=[C:8]([O:9][CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 5357283Methyl Ferulate

Product 1

HCID 20744699(E)-4-butoxy-3-methoxycinnamic acid methyl esterYield 183.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4.16 g (20.0 mmol) ferulic acid methyl ester was dissolved in 115 ml 2-butanone. 2.09 ml (22.0 mmol) η-butyl bromide and 11.06 g (80 mmol) potassium carbonate were added. The reaction suspension was then heated at reflux temperature for 20 hours. The reaction mixture was filtered. The filtrate was concentrated by evaporation. The crude product was recrystallised from 42 ml isopropyl alcohol and yielded 4.85 g (92%) (E)-4-butyloxy-3-methoxycinnamic acid methyl ester as white crystals.

Workup

  1. temperatureThe reaction suspension was then heated
  2. temperatureat reflux temperature for 20 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationThe filtrate was concentrated by evaporation
  5. customThe crude product was recrystallised from 42 ml isopropyl alcohol

Sources & evidence

ORD record
ord-864d5f41f4884797a9a0f8d5336cd914
Source dataset
uspto-grants-2004_12
Patent number
US06831148B2

Reaction notes

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