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

HRID 276800Notes

Reaction equation

HRID 276800 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>>[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

4

Reactant 3

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

Product 1

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

Conditions

Temperature
40 °C

Procedure

4-Formylcinnamic acid dimethyl acetal (Cleeland, Jr., et al., U.S. Pat. No. 3,969,373) (20.00 g) and anhydrous potassium carbonate (12.44 g) were stirred in anhydrous N,N-dimethylfornamide (189 ml) for 5 minutes. Methyl iodide (12.8 g) 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%), 1H-NMR (DMSO-d6) consistent with structure.

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-9ce82db5ae704ec1b35a9d0810a7d640
Source dataset
uspto-grants-2002_03
Patent number
US06355646B1

Reaction notes

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