Methanol → methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylate

HRID 390631Notes

Reaction equation

HRID 390631 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:18][CH2:19][CH3:20])/[C:15]([OH:17])=[O:16])[CH:9]=[CH:10][C:11]=1[I:12])[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.O.[CH3:27]O>>[CH2:1]([O:5][C:6]1[CH:7]=[C:8](/[CH:13]=[C:14](\[O:18][CH2:19][CH3:20])/[C:15]([O:17][CH3:27])=[O:16])[CH:9]=[CH:10][C:11]=1[I:12])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 68961569(Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylic acid

Product 1

HCID 86626090methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylateYield 61%

Procedure

In an Emrys Optimizer microwave reactor, 0.8 g (2 mmol) of (Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylic acid is dissolved in 10 mL of methanol and 1 mL of concentrated sulfuric acid and heated at 70° C. by microwave for 2 hours. After addition of water, the reaction medium is extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated. 0.5 g (61%) of methyl (Z)-3-(3-butoxy-4-iodophenyl)-2-ethoxyacrylate is obtained.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b4d3a86657794a0c8da4344e60d494dc
Source dataset
uspto-grants-2013_02
Patent number
US08383652B2

Reaction notes

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