Methyl iodide → (E)-methyl 3-(3-methoxyphenyl)acrylate

HRID 716013Notes

Reaction equation

HRID 716013 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.[C:14]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6376683-Methoxycinnamic Acid

Product 1

HCID 11041597(E)-methyl 3-(3-methoxyphenyl)acrylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (E)-3-(3-methoxyphenyl)acrylic acid (3.56 g, 20 mmol). K2CO3 (3.1 g, 22 mmol), and iodomethane (4.0 g, 28 mmol) in acetone (20 mL) was heated to 70° C. for 16 hours. The mixture was concentrated and partitioned between water and ethyl acetate to afford the crude title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between water and ethyl acetate

Sources & evidence

ORD record
ord-d04f77836ff34219b92b4a1192de63a6
Source dataset
uspto-grants-2015_11
Patent number
US09187483B2

Reaction notes

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