Butyl bromide → (E)-4-butoxy-3-methoxycinnamic acid methyl ester

HRID 1797342Notes

Reaction equation

HRID 1797342 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.[CH2:16](Br)[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:16]([O:12][C:11]1[CH:13]=[CH:14][C:6](/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:15])=[CH:7][C:8]=1[O:9][CH3:10])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 5357283Methyl Ferulate

Product 1

HCID 20744699(E)-4-butoxy-3-methoxycinnamic acid methyl esterYield 92%

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) n-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%) methyl (2E)-3-(4-butoxy-3-methoxyphenyl)-2-propenoate 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-09719e658f81494caa52bd7b513f6ea3
Source dataset
uspto-grants-2006_04
Patent number
US07034098B2

Reaction notes

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