Butyl bromide → HCID 67481110, compound

HRID 2308115Notes

Reaction equation

HRID 2308115 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>[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:14]=[CH:13][C:11]([O:12][CH2:16][CH2:17][CH2:18][CH3:19])=[C:8]([O:9][CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 5357283Methyl Ferulate

Product 1

HCID 67481110HCID 67481110, compound

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 yielded 4.85 g (92%) (4-butoxy-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-07b3acc7f94f471c9f93a7acd2cacb37
Source dataset
uspto-grants-2004_12
Patent number
US06833421B1

Reaction notes

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