Methyl iodide → (E)-methyl 4-(dimethoxymethyl)cinnamate

HRID 1955622Notes

Reaction equation

HRID 1955622 reaction equation
CO[C:3]([O:15][CH3:16])([OH:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][CH:7]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].[CH3:23]I>CN(C=O)C>[CH3:17][O:20][CH:12]([O:13][CH3:23])[C:9]1[CH:8]=[CH:7][C:6](/[CH:5]=[CH:4]/[C:3]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 865896714-Formylcinnamic acid dimethyl acetal

Product 1

HCID 23247180(E)-methyl 4-(dimethoxymethyl)cinnamateYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

4-Formylcinnamic acid dimethyl acetal (Cleeland, Jr., et al., U.S. Pat. No. 3,969,373; Jul. 13, 1976) (20.00 g, 90.00 mmol) and anhydrous potassium carbonate (12.44 g, 90.00 mmol) were stirred in anhydrous DMF (189 mL) for 5 minutes. Methyl iodide (12.8 g, 90.0 mmol) was added and the resulting mixture was stirred vigorously with gentle heating (oil bath at 40° C.) for 18 h. Volatiles were evaporated in vacuo and the residue partitioned between hexanes (400 mL) and water (100 mL). The hexanes layer was dried (magnesium sulfate) and evaporated to give (E)-methyl 4-(dimethoxymethyl)cinnamate as a pale yellow oil (18.98 g, 89%);

Workup

  1. customVolatiles were evaporated in vacuo
  2. customthe residue partitioned between hexanes (400 mL) and water (100 mL)
  3. dry with materialThe hexanes layer was dried (magnesium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-c3268e62f5c64c61934d98e90fc16e73
Source dataset
uspto-grants-1998_07
Patent number
US05776940

Reaction notes

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